Triphenylphosphine → HCID 57964946, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triphenylphosphine (1.41 g, 5.4 mmol) in tetrahydrofuran (50 mL) under argon was cooled to 0° C. Diisopropylcarbodiimide (1.06 mL, 5.4 mmol) was added dropwise, followed by 1-Boc-3-hydroxypiperidine (Alfa Aesar, Ward Hill, Mass., USA; 0.92 g, 4.6 mmol) and then 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 30; 0.55 g, 3.6 mmol). The mixture was stirred at room 0° C. for 4 h and the volatiles were then evaporated. The crude product was purified by silica gel chromatography, eluting with 16-20% ethyl acetate/hexanes to give 3-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (135 mg, 11%).

Provenance & Evidence