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_4031299
_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         'C23 H25 N5 O5 S2'
_chemical_formula_sum            'C23 H25 N5 O5 S2'
_chemical_formula_weight         515.60
_chemical_name_common
;
2-[[[4-[4-[(2-Diethylamino-5-nitropyrimidin-4-yl)amino]
phenoxy]phenyl]sulfonyl]methyl]thiirane 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 87.806(3)
_cell_angle_gamma                83.013(4)
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_cell_length_b                   12.992(2)
_cell_length_c                   16.159(3)
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_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.49
_cell_measurement_theta_min      2.93
_cell_volume                     1204.1(4)
_computing_cell_refinement       'Bruker SAINT v7.68A'
_computing_data_collection       'Bruker APEX-II v2010-7'
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker 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
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16135
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.469
_diffrn_reflns_theta_min         1.696
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADBS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             540
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_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.4615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3413
_reflns_number_total             4898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01044_si_002.cif
_cod_data_source_block           14
_cod_depositor_comments
'Adding full bibliography for 4031286--4031299.cif.'
_cod_original_cell_volume        1204.2(4)
_cod_database_code               4031299
_shelx_shelxl_version_number     2014/7