Sodium hydride → 3,4-dihydro-5-methyl-2-(4-pyridylmethyl)pyrimido[1,6-a]-indol-1(2H)-one hydrochloride

Participants

Reaction Steps

To a solution of 3,4-dihydro-5-methylpyrimido[1,6-a]-indol-1(2H)-one (188 mg) in N,N-dimethylformamide (3 ml) was added sodium hydride (60% in mineral oil, 88 mg) at 5° C. The mixture was stirred at the same temperature for 20 minutes. A solution of 4-chloromethylpyridine hydrochloride in N,N-dimethylformamide (3 ml) was added dropwise at 5° C. over five minutes. The reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 3 hours. The reaction mixture was diluted with chilled water and extract two times with 5%-methanol-chloroform. The extract was washed twice with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was dissolved in 1N-hydrochloric acid (10 ml) and evaporated in vacuo. The residue was pulverized with acetone to give 3,4-dihydro-5-methyl-2-(4-pyridylmethyl)pyrimido[1,6-a]-indol-1(2H)-one hydrochloride (160 mg).

Provenance & Evidence