Triethylamine → (3S,5S)-benzyl 3-(5-bromo-2-(methylthio)pyrimidin-4-ylamino)-5-methylpiperidine-1-carboxylate

Participants

Reaction Steps

A solution of 5-bromo-4-chloro-2-(methylthio)pyrimidine (1.0 g, 4.2 mmol), (3S,5S)-benzyl 3-amino-5-methylpiperidine-1-carboxylate (2.7 g, 8.35 mmol) and triethylamine 1.3 g, 12.5 mmol) in dioxane (50 ml) were stirred for 16 hours. The reaction was concentrated and the residue dissolved in methylene chloride (50 ml) and washed with water. The organic layer was dried and concentrated and purified on a silica gel column with 10-20% ethyl acetate/dichloromethane as solvent to give (3S,5S)-3-(5-bromo-2-methylsulfanyl-pyrimidin-4-ylamino)-5-methyl-piperidine-1-carboxylic acid benzyl ester as a viscous oil. MS (ES+): 452.

Provenance & Evidence