Synthesis of Diverse Substituted Pyrimidines through Cu Catalyst-Controlled Ts Group's Elimination and Reinsertion Pathway from 2H-Azirines with TosMICs
Cheng, Wen; Li, Mengfan; tang, hao; wang, yuxi; yu, qiurou; Bao, Xiaoli; Zhao, Yun-Hui; Yi, Weiyin; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01962A

data_7160938
_publ_section_title
;
 Synthesis of diverse substituted pyrimidines through Cu
 catalyst-controlled Ts group elimination and reinsertion pathway from
 2<i>H</i>-azirines with TosMICs.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2046
_journal_page_last               2060
_journal_paper_doi               10.1039/d5ob01962a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_sum            'C26 H24 N2 O2 S'
_chemical_formula_weight         428.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2nw9sn
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-07-02 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.613(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2932(15)
_cell_length_b                   14.2849(18)
_cell_length_c                   14.4944(16)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.30
_cell_volume                     2333.6(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            76409
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.598
_diffrn_reflns_theta_min         2.004
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.971
_exptl_transmission_factor_min   0.965
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4387
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0510P)^2^+1.2074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3592
_reflns_number_total             4387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01962a2.cif
_cod_data_source_block           mo_20250311A_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160938--7160939.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160938
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              44730