2,4-Dichloro-6-methoxy-3,5-triazine → HCID 86615299, compound

Participants

Reaction Steps

To a stirred solution of 2,4-dichloro-6-methoxy-1,3,5-triazine (10.0 g, 55.6 mmol, 1.0 equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (11.4 g, 55.6 mmol, 1.0 equiv) in acetonitrile (300 mL) was added drop by drop N-ethyl diisopropylamine (48.5 mL, 36.6 g, 278 mmol, 5.0 equiv) keeping the temperature below 25° C. After stirring the reaction mixture at rt for 16 h, the heterogeneous mixture was poured onto ice water and extracted three times with ethyl acetate. The combined organic layers were washed with brine and 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 to give 11.4 g (60%) of the title compound as a off-white foam. MS (ISP): 344.3 [M+H]+.

Provenance & Evidence