2-(Tributylstannyl)pyridine → 5-(4-Chloro-phenyl)-1-phenyl-6-(4-pyridin-2-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693522Notes

Reaction equation

HRID 1693522 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.C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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:4]=[CH:3][C:2]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:7][CH:6]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 20472026-(4-Bromophenyl)-5-(4-chlorophenyl)-1-phenyl-1H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-one

Product 1

HCID 115185335-(4-Chloro-phenyl)-1-phenyl-6-(4-pyridin-2-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 46%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A reaction tube charged with 6-(4-bromophenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (40.0 mg, 0.084 mmol) and Pd(PPh3)4 (9.7 mg, 0.0084 mmol) is purged with nitrogen. A solution of 2-tributylstannanyl-pyridine (61.6 mg, 0.168 mmol) in anhydrous toluene (1.0 mL) is added via syringe. The reaction mixture is heated at 100° C. overnight, and is partitioned between water and ethyl acetate. The organic phase is washed with brine, concentrated, and purified by preparative LCMS followed by silica gel chromatography to provide the title compound (18.4 mg, 46% yield) as a white solid product; HPLC-MS calculated for C28H18ClN5O (M+H+) 476.1. Found: 476.1.

Workup

  1. customis purged with nitrogen
  2. customis partitioned between water and ethyl acetate
  3. washThe organic phase is washed with brine
  4. concentrationconcentrated
  5. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-098150a7c1b2492d9c988ea7b506e1e7
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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