Benzyl Bromide → 1-(m-nitrophenyl)-3-benzylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

To a mixture of 2.8 g of 1-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4 (1H,3H)-dione and 30 ml of dry dimethylformamide was added 0.6 g of approximately 50 % sodium hydride. The mixture was stirred for 30 minutes at room temperature and for additional 10 minutes at a temperature of 70°-80°C. To the mixture was further added dropwise 3.4 g of benzyl bromide and stirring was continued for 30 minutes. The solvent was removed from the resulting mixture by distillation, and to the residue was added water to give a crude precipitate. This product was recrystallized from a mixture of methanol and dimethylformamide to yield 3.3 g of 1-(m-nitrophenyl)-3-benzylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione as pale yellow prisms, melting at 219°-220°C.

Provenance & Evidence