Water → HCID 57964907, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil; 6 mg, 0.15 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; 37 mg, 0.078 mmol) in anhydrous tetrahydrofuran (750 μL) under argon. Cyclopentanol (70 μL, 0.77 mmol) was added and the mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried (sodium sulfate), filtered, evaporated, and purified on an Isco 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 cyclopentyl ester (6 mg, 18%). Mass spectrum (ES) MH+=423.

Provenance & Evidence