Sodium Carbonate → 1-(1-methyl-3-piperidyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine acetate

Participants

Reaction Steps

A solution of racemic 3-iodo-1-(1-methyl-3-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.050 g, 0.00014 mol) in dimethoxyethane (2.5 mL) and water (5 mL) was treated with 4-phenoxyphenylboronic acid (0.033 g, 0.00015 mol), sodium carbonate (0.037 g, 0.00037 mol) and tetrakis (triphenylphosphine) palladium (0) (0.016 g, 0.000014 mol) at 80° C. for 18 hours. The organic solvent was removed in vacuo, and the crude material was purified by preparative RP-HPLC (Rainin C18, 8 μm, 300 A, 25 cm; 30% isocratic for five minutes, then 30%-60% acetonitrile-0.1M ammonium acetate over 15 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give 1-(1-methyl-3-piperidyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine acetate as a white solid (0.040 g, 0.00009 mol).

Provenance & Evidence