Regioselective Control of the SNAr Amination of 5-Substituted-2,4-Dichloropyrimidines Using Tertiary Amine Nucleophiles.
Lee, Mijoon; Rucil, Tomas; Hesek, Dusan; Oliver, Allen G.; Fisher, Jed F.; Mobashery, Shahriar; The Journal of organic chemistry 80 (2015) 7757–7763; doi:10.1021/acs.joc.5b01044

data_4031297
_publ_section_title
;
 Regioselective Control of the SNAr Amination of
 5-Substituted-2,4-Dichloropyrimidines Using Tertiary Amine Nucleophiles.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7757
_journal_page_last               7763
_journal_paper_doi               10.1021/acs.joc.5b01044
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H22 N4 O3'
_chemical_formula_sum            'C16 H22 N4 O3'
_chemical_formula_weight         318.37
_chemical_name_common
;
Ethyl 2-(4-morpholinyl)-6-propyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0826(7)
_cell_length_b                   14.2388(8)
_cell_length_c                   18.9958(12)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.52
_cell_measurement_theta_min      4.66
_cell_volume                     3268.1(3)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX-II v2014-5.0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42158
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.005
_diffrn_reflns_theta_min         3.104
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       rod
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin. Twin percentage: 0.63:0.37.
;
_refine_ls_abs_structure_Flack   0.37(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.4703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                5868
_reflns_number_total             6152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01044_si_002.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 4031286--4031299.cif.'
_cod_database_code               4031297
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.896
_shelx_estimated_absorpt_t_max   0.956
_diffrn_source_monochromator     'MONTEL Multi-layer'