Sodium hydride → 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]butyloxy}acetic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, to a solution of 763 mg of 5,6-diphenyl-2-(methylamino)pyrazine in 4 ml of N,N-dimethylformamide, 140 mg of 60% sodium hydride was added, followed by stirring at 80° C. for 30 minutes. The reaction solution was ice-cooled and a solution of 657 mg of 2-(4-bromobutyloxy)acetic acid methyl ester in 2 ml of N,N-dimethylformamide was slowly added. After an ice bath was removed, the mixture was stirred at room temperature for 14 hours. The reaction solution was combined with ice water and extracted with ethyl acetate and, after the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 240 mg of the desired compound as a pale yellow oily substance.

Provenance & Evidence