Benzylamine → 8-Cyclopentyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Participants

Reaction Steps

A mixture of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (9), (1 g, 4.2 mmol), 1.2 equivalent of cyanoacetic acid, and a catalytic amount of benzylamine was taken into acetic acid and refluxed for about 6 h. After completion of the reaction by TLC, the reaction mixture was cooled to room temperature and product precipitated from the reaction mixture. Additional product was precipitated from the reaction mixture via the addition of hexane. The resultant solid was collected, washed with saturated NaHCO3, water, and subsequently dried under vacuum. The resultant crude product (10) was recrystallized in 2-propanol.

Provenance & Evidence