Potassium Carbonate → 3-chloro-N-[3-(4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-ylmethoxy)-4-methyl-phenyl]-benzamide

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([OH:15])[CH:9]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]1[C:35]2[C:30](=[N:31][CH:32]=[N:33][C:34]=2[Cl:36])[N:29]([CH3:37])[N:28]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][CH2:26][C:27]2[C:35]3[C:30](=[N:31][CH:32]=[N:33][C:34]=3[Cl:36])[N:29]([CH3:37])[N:28]=2)[CH:9]=1)=[O:6]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 8375333-chloro-N-(3-hydroxy-4-methylphenyl)benzamide

HCID 575815813-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 575815933-chloro-N-[3-(4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-ylmethoxy)-4-methyl-phenyl]-benzamide

Procedure

A mixture of 3-chloro-N-(3-hydroxy-4-methyl-phenyl)-benzamide (100 mg, 0.38 mmol, 36721-253A) and potassium carbonate (63.1 mg, 0.45 mmol) was stirred at room temp for 30 minutes before 3-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (90.9 mg, 0.28 mmol, Example 5) was added. The reaction was stirred at room temperature overnight and then concentrated under reduced pressure to remove dimethylformamide. The residue was dissolved in ethyl acetate, washed with water, dried and concentrated. The crude product was either used directly in the next step (described in Example 11) or purified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40) to give pure 3-chloro-N-[3-(4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-ylmethoxy)-4-methyl-phenyl]-benzamide as a white solid. (Yield 33.3 mg).