Sodium Bicarbonate → HCID 44622155, compound

Participants

Reaction Steps

A mixture of 4-chloro-6-(2-methyl-pyridin-3-yloxy)-pyrimidine-5-carbaldehyde (Intermediate 18; 515 mg, 2.1 mmol) and 4-hydrazino-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 9; 688 mg, 3.2 mmol) in toluene (5 mL) was heated at reflux overnight. Aqueous sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate. The organic phases were evaporated and purified on an Isco 40 g column, eluting with 0-3% methanol/dichloromethane to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (330 mg, 38%).

Provenance & Evidence