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_4031286
_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         'C8 H11 Cl N4 O2'
_chemical_formula_sum            'C8 H11 Cl N4 O2'
_chemical_formula_weight         230.66
_chemical_name_common            4-Chloro-N,N-diethyl-5-nitro-2-pyrimidinamine
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
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_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_length_c                   12.7855(11)
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_cell_measurement_theta_min      3.65
_cell_volume                     1033.68(13)
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_computing_data_collection       'Bruker APEX-II v2011-4.1'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker APEX-I'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.914
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_diffrn_reflns_limit_l_min       -15
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_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.505
_diffrn_reflns_theta_min         3.646
_exptl_absorpt_coefficient_mu    3.199
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
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_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0718P)^2^+1.2651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3502
_reflns_number_total             3549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01044_si_002.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 4031286--4031299.cif.'
_cod_original_cell_volume        1033.68(12)
_cod_database_code               4031286
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.327
_shelx_estimated_absorpt_t_max   0.645