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_4031291
_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_formula_moiety         'C6 H7 Cl N4 O2'
_chemical_formula_sum            'C6 H7 Cl N4 O2'
_chemical_formula_weight         202.61
_chemical_name_common            4-Chloro-N,N-dimethyl-5-nitro-2-pyrimidinamine
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_gamma                90
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_cell_length_b                   3.775(2)
_cell_length_c                   23.807(14)
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_cell_measurement_theta_min      2.28
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_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0617
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_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
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_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
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_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5152
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
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_diffrn_reflns_theta_max         25.953
_diffrn_reflns_theta_min         1.860
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_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0965
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+40.5689P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.2320
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_reflns_number_gt                1301
_reflns_number_total             1589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01044_si_002.cif
_cod_data_source_block           3f-2
_cod_depositor_comments
'Adding full bibliography for 4031286--4031299.cif.'
_cod_original_cell_volume        1629.2(17)
_cod_database_code               4031291
_shelx_shelxl_version_number     2014/7