Water → N-(5-Nitro-pyrimidin-2-yl)-benzamide

Participants

Reaction Steps

Benzoyl chloride (0.92 ml, 7.93 mmol) was added dropwise to a stirred solution of 2-amino-5-nitropyrimidine (1.00 g, 7.14 mmol) in pyridine (20 ml) and the reaction was heated at reflux for 4 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature, poured into water (200 ml) and allowed to stand for 16 hours. The solid was collected by suction filtration, washed with water (3×20 ml) and dried in vacuo. An oil residue on the surface of the aqueous phase was dissolved in dichloromethane (50 ml) and then purified by flash chromatography on silica gel, eluting with 1–3% methanol in dichloromethane. The two materials were identical and yielded 2-(N-benzoyl)amino-5-nitropyrimidine (826 mg, 47% yield) as a white solid:

Provenance & Evidence