Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids
Blanca R. Díaz-Sánchez; Martín A. Iglesias-Arteaga; Roberto Melgar-Fernández; Eusebio Juaristi; Journal of Organic Chemistry 72 (2007) 4822–4825; doi:10.1021/jo0705115

data_4023954
_publ_contact_author_address
;     Departamento de Qu\'imica
      Centro de Investigaci\'on y de Estudios Avanzados
      Instituto Polit\'ecnico Nacional
      Apartado Postal 14-740      
      07000 M\'exico D.F.
      Mexico
;
_publ_contact_author_email       juaristi@relaq.mx
_publ_contact_author_fax         (+52)(55)57477132
_publ_contact_author_name        'Eusebio Juaristi'
_publ_contact_author_phone       (+52)(55)50613722
_publ_section_title
;
 Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones
 and Their Derivatization Utilizing the Sonogashira Coupling Reaction
 in the Enantioselective Synthesis of \a-Substituted
 \b-Amino Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4822
_journal_page_last               4825
_journal_paper_doi               10.1021/jo0705115
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C22 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40
_chemical_melting_point          522
_chemical_name_systematic
;

1-Benzoyl-2(S)-iso-propyl-5-phenylethynyl-2,3-dihydro-4(H)-pyrimidin-4-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-12-10
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.1010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   10.130(3)
_cell_length_b                   26.145(7)
_cell_length_c                   11.359(3)
_cell_measurement_reflns_used    5474
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.395
_cell_volume                     2825.2(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0822
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11115
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.41
_diffrn_standards_number         11115
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     728
_refine_ls_number_reflns         6523
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.156
_refine_ls_shift/su_mean         0.038
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                1965
_reflns_number_total             6523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705115si20070313_011453_3.cif
_cod_data_source_block           ejbd06
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023954