Cyclopentylamine → HCID 69654667, compound

Participants

Reaction Steps

To a solution of 0.150 g (0.36 mmol) of 4-[4-(7-amino-pyrido[2,3-d]pyrimidin-2-ylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (Example 13) in 2 mL of dimethylformamide, cooled in an ice bath, is added 0.022 g (0.54 mmol) of 60% sodium hydride. The cooled solution is stirred for 15 minutes, then treated with 0.088 g (0.54 mmol) of carbonyldiimidazole. The cooled solution is stirred for another 30 minutes, then treated with 0.071 mL (0.72 mmol) of cyclopentylamine. The resulting solution is stirred at room temperature for 1 hour, then added to cold water. The solid is collected by filtration to give a first crop of material. The aqueous filtrate is then extracted with dichloromethane, and the extracts are dried (magnesium sulfate) and concentrated to give a second crop of material. The 2 crops are combined and purified by flash chromatography, eluting with a gradient of 0% to 5% methanol/dichloromethane during 30 minutes to give 0.1159 g (60.4%) of the product as a solid.

Provenance & Evidence