Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C-H Arylation Reactions
Igor Čerňa; Radek Pohl; Blanka Klepetářová; Michal Hocek; Journal of Organic Chemistry 73 (2008) 9048–9054; doi:10.1021/jo8018126

data_4023865
_publ_contact_author_address
; 
Institute of Organic Chemistry and Biochemistry
Academy of Sciences of the Czech Republic
Flemingovo nam. 2
16010 Prague 6
Czech Republic
;
_publ_contact_author_email       hocek@uochb.cas.cz
_publ_contact_author_fax         '+420 220183559'
_publ_contact_author_name        'Michal Hocek'
_publ_contact_author_phone       '+420 220183324'
_publ_section_title
;
 Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines
 by a Combination of the Suzuki Cross-coupling,
 N-Arylation, and Direct C-H Arylation Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9048
_journal_page_last               9054
_journal_paper_doi               10.1021/jo8018126
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H27 F1 N4 O3'
_chemical_formula_sum            'C29 H27 F N4 O3'
_chemical_formula_weight         498.56
_chemical_name_systematic
6-(3-fluoro-4-methoxyphenyl)-9-isopropyl-2,8-bis(4-methoxyphenyl)-9H-purine
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-07-30
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.10040(10)
_cell_length_b                   17.4319(2)
_cell_length_c                   19.7015(2)
_cell_measurement_reflns_used    21093
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     2438.52(5)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38154
_diffrn_reflns_theta_full        74.532
_diffrn_reflns_theta_max         76.837
_diffrn_reflns_theta_min         4.489
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details 'Flack (1983), 2084 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.05(16)
_refine_ls_extinction_coef       25(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0768
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000369
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 3.49 1.31 2.10 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0430
_refine_ls_wR_factor_gt          0.0360
_refine_ls_wR_factor_ref         0.0360
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                3587
_reflns_number_total             4993
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            jo8018126_si_001.cif
_cod_data_source_block           CRYSTALS_cif
_cod_original_formula_sum        'C29 H27 F1 N4 O3'
_cod_database_code               4023865