Hydrochloric Acid → HCID 57929461, compound

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (1.68 g, 6.40 mmol) was added, at RT, to a solution of 5-azido-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.29 g, 4.27 mmol) in THF (43 mL) and the reaction mixture was stirred at 35° C. for 2 h. An HCl (1 M, 22 mL) was then added and the reaction mixture was heated at reflux for 2 h and then was stored at 4° C. overnight. The resulting mixture was neutralized to pH 8 with NaHCO3 (sat'd aq), and was extracted with EtOAc (2×200 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (from 2 to >5% MeOH/DCM in 20 min.) to give 0.89 g (75% yield) of 5-amino-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid. MS=277 [M+1]+.

Provenance & Evidence