Water → HCID 57964969, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil; 10 mg, 0.25 mmol) was added to a solution of 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid 4-nitro-phenyl ester (Example 123; 60 mg, 0.13 mmol) in anhydrous tetrahydrofuran (1 mL) under argon. The mixture was stirred for 5 min and then cyclobutanol (11 μL, 0.14 mmol) was added and the mixture was stirred at room temperature for 7 h. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate), filtered, evaporated, and purified on a Silicycle 4 g column, eluting with 0-4% methanol/dichloromethane to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid cyclobutyl ester (7 mg, 14%).

Provenance & Evidence