Water → HCID 57964982, compound

Participants

Reaction Steps

4-Nitrophenyl chloroformate (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 268 mg, 1.33 mmol) was added in three portions to a cooled (˜0° C.) solution of 4-(2-methyl-pyridin-3-yloxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 28; 275 mg, 0.89 mmol), and diisopropylethylamine (390 μL, 2.2 mmol) in anhydrous dichloromethane (10 mL). The mixture was warmed to room temperature and stirred for 1 h. Water (10 mL) was added, the layers were separated and the organic layer was washed with brine, dried (sodium sulfate), filtered, evaporated, and purified on a 23 g Supelco column, eluting with 0-7% methanol/dichloromethane to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid 4-nitro-phenyl ester (180 mg, 43%) as a white foam.

Provenance & Evidence