Cesium carbonate → 3-[6-[4-(6-Amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl}-benzonitrile (2, 1.00 g, 1.81 mmol) in N,N-dimethylformamide (25 mL) is degassed with argon for 0.5 h. Then 2-amino-5-bromopyridine (0.47 g, 2.72 mmol), cesium carbonate (1.18 g, 3.62 mmol), Pd(dppf)2Cl2 (0.147 g, 0.181 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 100° C. for 2 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3×). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by preparative HPLC to afford 3-[6-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile (3). LC-MS calculated for C29H18ClN7O (M+H+) 516.1, found 516.1.

Provenance & Evidence