Carbon Dioxide → tert-butyl 4-(6-(4-aminophenyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

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Reaction Steps

A solution of tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (0.13 g, 0.24 mmol) in tetrahydrofuran (5 mL) was degassed by the addition of crushed solid carbon dioxide. Palladium-on-carbon (5%, 20 mg) was then added. The mixture was stirred magnetically overnight under a balloon of hydrogen gas. The mixture was filtered through a pad of diatomaceous earth, eluting with ethyl acetate. The filtrate was concentrated under reduced pressure to provide tert-butyl 4-(6-(4-aminophenyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate as a pale yellow foam. MS (ES+): 506.4 (M+H)+

Provenance & Evidence