Sodium Cyanide → 3-cyanopropyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Participants

Reaction Steps

Heat a solution of 3-chloropropyl 2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylate (0.42 g; 1.0 equiv; 1.09 mmoles) and and sodium cyanide (0.085 g; 1.6 equiv; 1.73 mmoles) in dimethylformamide (3 mL) to 100° C. for 2 hours. Cool the mixture to ambient temperature, dilute with dichloromethane (20 mL) and wash the reaction mixture with water (25 mL). Extract the aqueous layer with dichloromethane (2×20 mL). Dry the combined organic extracts over sodium sulfate, filter, and concentrate to afford crude product. Combine the crude product and purify by column chromatography (0 to 10% methanol in dichloromethane) to afford 3-cyanopropyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate as a light brown oil and used in next step. MS (m/z): 378 (M+1).

Provenance & Evidence