tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate → tert-butyl 4-[4-amino-3-(4-aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (5.0 g, 0.0092 mol) in terahydrofuran (150 mL) 10% palladium on carbon (1.0 g) was added and the reaction mixture was hydrogenated on a Parr shaker over 96 hours. The catalyst was removed by filtration through a Celite pad and the filtrate was concentrated under reduced pressure. The residue was triturated in n-heptane and the precipitate was collected by filtration and dried to yield tert-butyl 4-[4-amino-3-(4-aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (2.51 g, 0.0061 mol) as an off-white solid.

Provenance & Evidence