Trifluoroacetic acid → HCID 58972425, compound

Participants

Reaction Steps

To a stirred solution of 4-(5-cyanomethoxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.67 g, 2.0 mmol, 1.0 equiv) in dichloromethane (15 mL) was added drop by drop 90% trifluoroacetic acid (1.82 mL, 2.55 g, 20 mmol, 10 equiv) and the reaction was stirred at rt for 16 h. The reaction mixture was evaporated and the residue partitioned between water and dichloromethane. The pH of the water phase was adjusted to 9-10 by addition of a sat. solution of potassium carbonate and the mixture extracted three times with dichloromethane. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol (+25% ammonia in water) to give 0.32 g (69%) of the title compound as colorless oil. MS (ISP): 234.0 [M+H]+.

Provenance & Evidence