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_4031298
_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 H24 N4 O6 S2'
_chemical_formula_sum            'C23 H24 N4 O6 S2'
_chemical_formula_weight         516.58
_chemical_name_common
;
2-[[[4-[4-[(2-Diethylamino-5-nitropyrimidin-4-yl)oxy]phenoxy]phenyl]
sulfonyl]methyl]thiirane
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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_symmetry_space_group_name_Hall  '-P 1'
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_diffrn_ambient_temperature      121(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0175
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_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_max 0.996
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_diffrn_reflns_theta_max         27.463
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_exptl_absorpt_coefficient_mu    0.265
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_exptl_absorpt_correction_T_min  0.7035
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_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 2008)'
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0526
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.6591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1223
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_reflns_number_gt                4706
_reflns_number_total             5574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01044_si_002.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 4031286--4031299.cif.'
_cod_original_cell_volume        1221.50(18)
_cod_database_code               4031298
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.979