(R)-tert-Butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Uses

N-Boc-Ibrutinib is an impurity of Ibrutinib (I124970), which is a highly selective Bruton’s tyrosine kinase (Btk) irreversible inhibitor.

Synthesis

3-(4-phenoxyphenyl) lH-pyrazolo [3,4-d] pyrimidin-4-amine (1.14g, 3.76mmol)was dissolved DMF (30mL) in, and then the reaction solution was added (S)-tert-butyl 3-((methylsulfonyl) oxy) piperidine-1-carboxylate (4.2g, 15.04mmol), cesium carbonate(0.64mL, 8.21 mmol), 4- dimethylaminopyridine pyridine (3.67g, 11.28mmol). Was stirred at 90 ℃, the reaction was completed, distilled under reduced pressure of DMF, and extracted with dichloromethane (150mL × 3), brine (60mL), dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure, the crude product was silica gel column Analysis of separation and purification (methylene chloride /methanol (V / V) = 40/1), to give the product (R)-tert-Butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (1.28 g, 70 percent).