Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C-H Arylation Reactions
Igor Čerňa; Radek Pohl; Blanka Klepetářová; Michal Hocek; Journal of Organic Chemistry 73 (2008) 9048–9054; doi:10.1021/jo8018126

data_4023866
_publ_contact_author_address
; 
Institute of Organic Chemistry and Biochemistry
Academy of Sciences of the Czech Republic
Flemingovo nam. 2
16010 Prague 6
Czech Republic
;
_publ_contact_author_email       hocek@uochb.cas.cz
_publ_contact_author_fax         '+420 220183559'
_publ_contact_author_name        'Michal Hocek'
_publ_contact_author_phone       '+420 220183324'
_publ_section_title
;
 Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines
 by a Combination of the Suzuki Cross-coupling,
 N-Arylation, and Direct C-H Arylation Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9048
_journal_page_last               9054
_journal_paper_doi               10.1021/jo8018126
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C21 H21 N5 O4, C H Cl3'
_chemical_formula_sum            'C22 H22 Cl3 N5 O4'
_chemical_formula_weight         526.81
_chemical_name_systematic
9-(4-methoxyphenyl)-8-(3,4,5-trimethoxyphenyl)-9H-purin-6-amine
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-08-13
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 91.195(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1515(12)
_cell_length_b                   13.1309(11)
_cell_length_c                   18.5570(17)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    298
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     2473.1(4)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29663
_diffrn_reflns_theta_full        73.710
_diffrn_reflns_theta_max         78.414
_diffrn_reflns_theta_min         4.125
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.687
_exptl_absorpt_correction_T_max  0.51
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       41(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1339
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000254
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 6.72 0.893 4.57 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0780
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0567
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                2510
_reflns_number_total             5219
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            jo8018126_si_002.cif
_cod_data_source_block           CRYSTALS_cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023866