Triphenylphosphine → 3-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Boc-3-hydroxypiperidine (Alfa Aesar, Ward Hill, Mass., USA; 80 mg, 0.4 mmol) and triphenylphosphine (136 mg, 0.52 mmol) were added to a solution of 4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 31; 100 mg, 0.34 mmol) in tetrahydrofuran (1 mL). The mixture was cooled to 0° C., and then diisopropylazodicarboxylate (102 μL, 0.52 mmol) was added. The mixture was stirred overnight, then silica gel (˜500 mg) was added, the solvents were evaporated and the product was eluted from a silica gel column with 50% ethyl acetate/hexanes to give 3-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (10.5 mg, 6.5%) as a solid.

Provenance & Evidence