The synthesis of carbonyl 2-amino-pyrimidines via tandem regioselective heterocyclization of 1,3-diynes with guanidine and selective oxidation
Liang Zhang; Mingzhu Zhao; Xiaoming Zhao; Chem.Commun. 51 (2015) 9370–; doi:10.1039/C5cc02238J

data_7117212
_publ_section_title
;
 The synthesis of carbonyl 2-amino-pyrimidines via tandem regioselective
 heterocyclization of 1,3-diynes with guanidine and selective oxidation
;
_journal_name_full               Chem.Commun.
_journal_page_first              9370
_journal_paper_doi               10.1039/C5cc02238J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C17 H13 N3 O'
_chemical_formula_weight         275.30
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/cc13zlc1
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-06 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.267(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2120(10)
_cell_length_b                   17.471(3)
_cell_length_c                   15.196(3)
_cell_measurement_reflns_used    3536
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.68
_cell_volume                     1382.6(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9321
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.739
_diffrn_reflns_theta_min         1.777
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0986P)^2^+0.1823P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1547
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2364
_reflns_number_total             2932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc02238j2.cif
_cod_data_source_block           mo_41009a
_cod_original_cell_volume        1382.6(5)
_cod_database_code               7117212
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2013-2
_shelx_res_checksum              66184