Related literature {#sec1}
==================

The title compound was prepared according to a modification of the procedure of Fiorini & Abel (1998[@bb2]).  For the synthesis and/or biological activity of related compounds, see: Legraverend & Grierson (2006[@bb4]).  For related structures, see: Kubicki & Codding (2001[@bb3]); Trávníček & Popa (2007[@bb11]); Rouchal *et al.* ( 2009*a* [@bb7],*b* [@bb8],*c* [@bb9]). 

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~10~H~14~ClN~5~*M* *~r~* = 239.71Monoclinic,*a* = 12.0483 (3) Å*b* = 8.7689 (2) Å*c* = 11.5538 (3) Åβ = 109.965 (3)°*V* = 1147.30 (5) Å^3^*Z* = 4Mo *K*α radiationμ = 0.31 mm^−1^*T* = 120 K0.40 × 0.40 × 0.30 mm

### Data collection {#sec2.1.2}

Oxford Diffraction Xcalibur (Sapphire2 large Be window) diffractometerAbsorption correction: multi-scan (*CrysAlis RED*; Oxford Diffraction, 2009[@bb6]) *T* ~min~ = 0.968, *T* ~max~ = 1.00013393 measured reflections2022 independent reflections1798 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.016

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.025*wR*(*F* ^2^) = 0.068*S* = 1.052022 reflections149 parametersH-atom parameters constrainedΔρ~max~ = 0.21 e Å^−3^Δρ~min~ = −0.18 e Å^−3^

 {#d5e475}

Data collection: *CrysAlis CCD* (Oxford Diffraction, 2009[@bb6]); cell refinement: *CrysAlis RED* (Oxford Diffraction, 2009[@bb6]); data reduction: *CrysAlis RED*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb10]); molecular graphics: *ORTEP-3* (Farrugia, 1997[@bb1]) and *Mercury* (Macrae *et al.*,  2008[@bb5]); software used to prepare material for publication: *SHELXL97*. 

Supplementary Material
======================

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536810011797/pk2238sup1.cif](http://dx.doi.org/10.1107/S1600536810011797/pk2238sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536810011797/pk2238Isup2.hkl](http://dx.doi.org/10.1107/S1600536810011797/pk2238Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?pk2238&file=pk2238sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?pk2238sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?pk2238&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [PK2238](http://scripts.iucr.org/cgi-bin/sendsup?pk2238)). 

The financial support of this work by the Czech Ministry of Education, project No.  MSM 7088352101 is gratefully acknowledged. 

Comment
=======

The heterocyclic system, imidazo\[4,5-*d*\]pyrimidine, commonly known as purine, was first named by Emil Fisher at the turn of the 19^th^ century.  A large number of variously substituted purines exhibit a wide range of biological activities (Legraverend & Grierson, 2006).  They act as interferon inducers, adenosine receptor ligands, inhibitors of microtubule assembly, protein kinases, sulfotransferases and phosphodiesterases.  The title molecule was prepared as a part of our research into the synthesis of novel trisubstituted purines. 

The asymmetric unit of the title compound consists of a single purine molecule.  Both imidazole and pyrimidine rings are nearly planar with maximum deviations from the mean plane being 0.0013 (14) Å for C4 (imidazole ring) and 0.0207 (13) Å for C2 (pyrimidine ring).  Both carbon atoms of the dimethylamino substituent lie essentially in the pyrimidine mean plane as demonstrated by torsion angles C3---C2---N5---C7 and C3---C2---N5---C6, which are 4.3 (2)° and 175.90 (13)°, respectively.  The torsion angle describing the orientation of isopropyl and purine ring, H8A---C8---N4---C4 is -163.55 (13)°.  Molecules are linked into chains along the *c* axis by weak C4---H4···N1 interactions (Table 1, Fig.  2).  Crystal packing is further stabilised by short C---H···N and C---H···Cl contacts (Table 1). 

Experimental {#experimental}
============

The title compound was prepared according to a slightly modified literature procedure (Fiorini & Abel, 1998).  2,6-Dichloro-9-(propan-2-yl)-9*H*-purine (0.87 mmol, 196 mg) and methylamine hydrochloride (0.91 mmol, 61.5 mg) were dissolved in a mixture of DMF (2.5 ml) and *N*-ethyl-*N*-isopropylpropan-2-amine (1.74 mmol, 225 mg).  The resulting solution was stirred at 90 °C for 2 hours.  Subsequently, the mixture was diluted with water and extracted with diethyl ether.  Combined organic layers were washed twice with brine and dried over Na~2~SO~4~. Crude product consisting of two compounds with relative abundances of 43% and 57% according to GC were obtained after evaporation of the solvent in vacuum.  The products were identified as *N*-methyl and *N*,*N*-dimethyl derivatives.  Column chromatography (silica gel; petroleum ether/ethyl acetate, v/v, 1/1) yielded the latter as a colourless crystalline powder (105 mg, 54%, mp 418--422 K).  The crystal used for data collection was grown by spontaneous evaporation from deuterochloroform at room temperature. 

Figures
=======

![ An ellipsoid plot (50% probability) of the asymmetric unit.  Hydrogen atoms are represented as arbitrary spheres.](e-66-o1016-fig1){#Fap1}

![ A view of the crystal structure showing chains parallel to the a-axis linked via C---H···N contacts (dotted lines).  H-atoms (except those which are involved in H-bonding) have been omitted for clarity.](e-66-o1016-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------- ---------------------------------------
  C~10~H~14~ClN~5~          *F*(000) = 504
  *M~r~* = 239.71           *D*~x~ = 1.388 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Melting point = 422--418 K
  Hall symbol: -P 2ybc      Mo *K*α radiation, λ = 0.7107 Å
  *a* = 12.0483 (3) Å       Cell parameters from 8720 reflections
  *b* = 8.7689 (2) Å        θ = 2.9--27.3°
  *c* = 11.5538 (3) Å       µ = 0.31 mm^−1^
  β = 109.965 (3)°          *T* = 120 K
  *V* = 1147.30 (5) Å^3^    Block, colourless
  *Z* = 4                   0.40 × 0.40 × 0.30 mm
  ------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------------------------ --------------------------------------
  Oxford Diffraction Xcalibur (Sapphire2 large Be window) diffractometer         2022 independent reflections
  Radiation source: Enhance (Mo) X-ray Source                                    1798 reflections with *I* \> 2σ(*I*)
  graphite                                                                       *R*~int~ = 0.016
  Detector resolution: 8.4 pixels mm^-1^                                         θ~max~ = 25.0°, θ~min~ = 2.9°
  ω scans                                                                        *h* = −14→13
  Absorption correction: multi-scan (*CrysAlis RED*; Oxford Diffraction, 2009)   *k* = −9→10
  *T*~min~ = 0.968, *T*~max~ = 1.000                                             *l* = −13→13
  13393 measured reflections                                                     
  ------------------------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.025   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.068                  H-atom parameters constrained
  *S* = 1.05                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0355*P*)^2^ + 0.4207*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  2022 reflections                      (Δ/σ)~max~ \< 0.001
  149 parameters                        Δρ~max~ = 0.21 e Å^−3^
  0 restraints                          Δρ~min~ = −0.18 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental.  CrysAlis RED (Oxford Diffraction Ltd, 2009).  Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 
  Geometry.  All esds (except the esd in the dihedral angle between two l.s.  planes) are estimated using the full covariance matrix.  The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry.  An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s.  planes. 
  Refinement.  Refinement of *F*^2^ against ALL reflections.  The weighted *R*-factor wR and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) etc.  and is not relevant to the choice of reflections for refinement. * R*-factors based on *F*^2^ are statistically about twice as large as those based on *F*, and *R*- factors based on ALL data will be even larger. 
  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- --------------- -------------- -------------------- --
         *x*            *y*             *z*            *U*~iso~\*/*U*~eq~   
  Cl1    0.78721 (3)    0.18146 (4)     0.33908 (3)    0.02432 (12)         
  N1     0.80758 (9)    −0.04481 (12)   0.48883 (9)    0.0166 (2)           
  N2     0.67313 (9)    0.15775 (12)    0.49228 (10)   0.0179 (3)           
  N3     0.69089 (10)   −0.14494 (13)   0.72589 (10)   0.0225 (3)           
  N4     0.82037 (10)   −0.23853 (13)   0.64258 (10)   0.0184 (3)           
  N5     0.55582 (10)   0.16106 (13)    0.61327 (10)   0.0197 (3)           
  C1     0.75175 (11)   0.08580 (15)    0.45552 (11)   0.0168 (3)           
  C2     0.63956 (11)   0.09009 (15)    0.58130 (11)   0.0169 (3)           
  C3     0.69562 (11)   −0.04950 (15)   0.63134 (11)   0.0167 (3)           
  C4     0.76612 (12)   −0.25408 (16)   0.72857 (13)   0.0229 (3)           
  H4A    0.7816         −0.3366         0.7851         0.027\*              
  C5     0.77572 (11)   −0.10713 (15)   0.57988 (11)   0.0157 (3)           
  C6     0.51096 (13)   0.30962 (16)    0.56040 (14)   0.0256 (3)           
  H6A    0.4933         0.3068          0.4711         0.038\*              
  H6B    0.5707         0.3880          0.5968         0.038\*              
  H6C    0.4388         0.3337          0.5778         0.038\*              
  C7     0.51768 (12)   0.10497 (17)    0.71274 (13)   0.0248 (3)           
  H7A    0.5191         −0.0068         0.7134         0.037\*              
  H7B    0.4372         0.1406          0.6998         0.037\*              
  H7C    0.5711         0.1435          0.7917         0.037\*              
  C8     0.90697 (12)   −0.34193 (16)   0.61883 (13)   0.0214 (3)           
  H8A    0.9468         −0.2849         0.5691         0.026\*              
  C9     0.84438 (14)   −0.47859 (18)   0.54375 (14)   0.0314 (4)           
  H9A    0.7866         −0.4433         0.4660         0.047\*              
  H9B    0.8038         −0.5358         0.5904         0.047\*              
  H9C    0.9024         −0.5447         0.5265         0.047\*              
  C10    1.00104 (13)   −0.38877 (18)   0.73954 (14)   0.0294 (3)           
  H10A   1.0359         −0.2974         0.7868         0.044\*              
  H10B   1.0627         −0.4476         0.7221         0.044\*              
  H10C   0.9650         −0.4515         0.7874         0.044\*              
  ------ -------------- --------------- -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------ ------------ -------------- -------------- -------------- --------------
        *U*^11^      *U*^22^      *U*^33^        *U*^12^        *U*^13^        *U*^23^
  Cl1   0.0311 (2)   0.0225 (2)   0.02385 (19)   0.00422 (14)   0.01520 (15)   0.00769 (13)
  N1    0.0180 (5)   0.0170 (6)   0.0149 (5)     −0.0002 (4)    0.0058 (4)     0.0005 (4)
  N2    0.0189 (6)   0.0173 (6)   0.0176 (5)     0.0002 (4)     0.0062 (4)     −0.0005 (4)
  N3    0.0256 (6)   0.0227 (6)   0.0219 (6)     0.0007 (5)     0.0115 (5)     0.0038 (5)
  N4    0.0198 (6)   0.0168 (6)   0.0189 (6)     0.0020 (4)     0.0071 (5)     0.0037 (5)
  N5    0.0196 (6)   0.0200 (6)   0.0204 (6)     0.0021 (5)     0.0081 (5)     −0.0020 (5)
  C1    0.0192 (7)   0.0170 (7)   0.0136 (6)     −0.0023 (5)    0.0046 (5)     −0.0003 (5)
  C2    0.0162 (6)   0.0174 (7)   0.0152 (6)     −0.0031 (5)    0.0031 (5)     −0.0048 (5)
  C3    0.0169 (6)   0.0174 (7)   0.0155 (6)     −0.0025 (5)    0.0049 (5)     −0.0019 (5)
  C4    0.0267 (7)   0.0221 (8)   0.0219 (7)     0.0014 (6)     0.0109 (6)     0.0067 (6)
  C5    0.0149 (6)   0.0153 (7)   0.0149 (6)     −0.0017 (5)    0.0025 (5)     −0.0016 (5)
  C6    0.0264 (7)   0.0228 (8)   0.0280 (8)     0.0070 (6)     0.0097 (6)     −0.0013 (6)
  C7    0.0231 (7)   0.0284 (8)   0.0276 (7)     −0.0006 (6)    0.0148 (6)     −0.0038 (6)
  C8    0.0202 (7)   0.0212 (7)   0.0250 (7)     0.0051 (6)     0.0105 (6)     0.0055 (6)
  C9    0.0347 (9)   0.0262 (8)   0.0329 (8)     0.0061 (7)     0.0110 (7)     −0.0036 (7)
  C10   0.0225 (7)   0.0306 (8)   0.0326 (8)     0.0044 (6)     0.0064 (6)     0.0094 (7)
  ----- ------------ ------------ -------------- -------------- -------------- --------------

Geometric parameters (Å, °) {#tablewrapgeomlong}
===========================

  ---------------- ------------- ------------------- -------------
  Cl1---C1         1.7575 (13)   C6---H6A            0.9800
  N1---C1          1.3174 (17)   C6---H6B            0.9800
  N1---C5          1.3522 (17)   C6---H6C            0.9800
  N2---C1          1.3230 (17)   C7---H7A            0.9800
  N2---C2          1.3630 (17)   C7---H7B            0.9800
  N3---C4          1.3112 (18)   C7---H7C            0.9800
  N3---C3          1.3926 (17)   C8---C9             1.520 (2)
  N4---C5          1.3696 (17)   C8---C10            1.5228 (19)
  N4---C4          1.3698 (18)   C8---H8A            1.0000
  N4---C8          1.4769 (17)   C9---H9A            0.9800
  N5---C2          1.3402 (17)   C9---H9B            0.9800
  N5---C7          1.4610 (18)   C9---H9C            0.9800
  N5---C6          1.4618 (18)   C10---H10A          0.9800
  C2---C3          1.4220 (19)   C10---H10B          0.9800
  C3---C5          1.3900 (18)   C10---H10C          0.9800
  C4---H4A         0.9500                            
                                                     
  C1---N1---C5     109.04 (11)   N5---C6---H6C       109.5
  C1---N2---C2     117.66 (11)   H6A---C6---H6C      109.5
  C4---N3---C3     104.13 (11)   H6B---C6---H6C      109.5
  C5---N4---C4     105.59 (11)   N5---C7---H7A       109.5
  C5---N4---C8     126.37 (11)   N5---C7---H7B       109.5
  C4---N4---C8     128.02 (11)   H7A---C7---H7B      109.5
  C2---N5---C7     121.94 (11)   N5---C7---H7C       109.5
  C2---N5---C6     120.29 (11)   H7A---C7---H7C      109.5
  C7---N5---C6     117.26 (11)   H7B---C7---H7C      109.5
  N1---C1---N2     132.14 (12)   N4---C8---C9        110.23 (11)
  N1---C1---Cl1    113.90 (10)   N4---C8---C10       110.34 (11)
  N2---C1---Cl1    113.95 (10)   C9---C8---C10       112.28 (12)
  N5---C2---N2     116.82 (12)   N4---C8---H8A       107.9
  N5---C2---C3     125.83 (12)   C9---C8---H8A       107.9
  N2---C2---C3     117.35 (11)   C10---C8---H8A      107.9
  C5---C3---N3     109.72 (11)   C8---C9---H9A       109.5
  C5---C3---C2     116.22 (12)   C8---C9---H9B       109.5
  N3---C3---C2     134.05 (12)   H9A---C9---H9B      109.5
  N3---C4---N4     114.04 (12)   C8---C9---H9C       109.5
  N3---C4---H4A    123.0         H9A---C9---H9C      109.5
  N4---C4---H4A    123.0         H9B---C9---H9C      109.5
  N1---C5---N4     125.94 (12)   C8---C10---H10A     109.5
  N1---C5---C3     127.51 (12)   C8---C10---H10B     109.5
  N4---C5---C3     106.52 (11)   H10A---C10---H10B   109.5
  N5---C6---H6A    109.5         C8---C10---H10C     109.5
  N5---C6---H6B    109.5         H10A---C10---H10C   109.5
  H6A---C6---H6B   109.5         H10B---C10---H10C   109.5
  ---------------- ------------- ------------------- -------------

Hydrogen-bond geometry (Å, °) {#tablewraphbondslong}
=============================

  -------------------- --------- --------- ------------- ---------------
  *D*---H···*A*        *D*---H   H···*A*   *D*···*A*     *D*---H···*A*
  C4---H4A···N1^i^     0.95      2.49      3.3728 (18)   154
  C7---H7C···Cl1^ii^   0.98      2.91      3.5981 (14)   128
  C7---H7B···N3^iii^   0.98      2.75      3.584 (2)     143
  C9---H9A···N3^iv^    0.98      2.73      3.6664 (18)   161
  -------------------- --------- --------- ------------- ---------------

Symmetry codes: (i) *x*, −*y*−1/2, *z*+1/2; (ii) *x*, −*y*+1/2, *z*+1/2; (iii) −*x*+1, *y*+1/2, −*z*+3/2; (iv) *x*, −*y*−1/2, *z*−1/2. 

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*          *D*---H   H⋯*A*   *D*⋯*A*       *D*---H⋯*A*
  -------------------- --------- ------- ------------- -------------
  C4---H4*A*⋯N1^i^     0.95      2.49    3.3728 (18)   154
  C7---H7*C*⋯Cl1^ii^   0.98      2.91    3.5981 (14)   128
  C7---H7*B*⋯N3^iii^   0.98      2.75    3.584 (2)     143
  C9---H9*A*⋯N3^iv^    0.98      2.73    3.6664 (18)   161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .