Water → HCID 25122893, compound

Participants

Reaction Steps

A solution of 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 92; 50 mg, 0.12 mmol) in a mixture of trifluoroacetic acid (0.5 mL) and dichloromethane (2 mL) was stirred at room temperature for 30 min, then the solvents were evaporated and the residue held under high vacuum. Dichloromethane (4 mL) was added, followed successively by benzyl chloroformate (26 μL, 0.18 mmol) and triethylamine (110 μL, 0.8 mmol). The mixture was stirred overnight at room temperature. Water was added and the mixture was extracted with three times with dichloromethane. The combined dichloromethane layers were evaporated and the residue was purified by C18 reversed phase HPLC using a gradient of 10-100% acetonitrile/water to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid benzyl ester (16 mg, 29%) as a white powder. HRMS Calcd. For C24H25N6O3 (MH+): 445.1983. Found: 445.1981.

Provenance & Evidence