Imidazole → 5-(4-Chloro-phenyl)-6-(4-imidazol-1-yl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693521Notes

Reaction equation

HRID 1693521 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:10](=[O:23])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1.CN[C@H]1[C@H](NC)CCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:9]2[C:10](=[O:23])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]=3[N:13]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([N:31]3[CH:35]=[CH:34][N:33]=[CH:32]3)=[CH:3][CH:4]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 62657Potassium Phosphate, TribasicHCID 20472026-(4-Bromophenyl)-5-(4-chlorophenyl)-1-phenyl-1H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-oneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 116626915-(4-Chloro-phenyl)-6-(4-imidazol-1-yl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 81%

Conditions

Temperature
100 °C

Procedure

A reaction tube charged with 6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (100.0 mg, 0.209 mmol), imidazole (85.5 mg, 1.26 mmol), Cul (4.0 mg, 0.021 mmol), (1R, 2R)-diaminomethylcyclohexane (6.0 mg, 0.042 mmol), and K3PO4 (88.9 mg, 0.429 mmol) is purged with nitrogen. Anhydrous 1,4-dioxane (4.0 mL) is added via syringe. The reaction mixture is heated at 100° C. for 5 days, and is partitioned between saturated NH4Cl aqueous solution and ethyl acetate. The organic phase is washed with brine, dried over MgSO4, concentrated, and purified by silica gel chromatography to provide the title compound (78.7 mg, 81% yield) as a white solid product; 1HNMR (CDCl3, 400 MHz) δ 8.91 (s, 1H), 8.35 (s, 1H), 8.10 (dd, 2H), 7.59 (d, 2H), 7.52 (m, 3H), 7.44-7.36 (m, 6H), 7.13 (d, 2H); HPLC-MS calculated for C26H17ClN6O (M+H+) 465.1. Found: 465.1.

Workup

  1. customis purged with nitrogen
  2. additionAnhydrous 1,4-dioxane (4.0 mL) is added via syringe
  3. customis partitioned between saturated NH4Cl aqueous solution and ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-187fe3909d064e6a86e81f4b085037d8
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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