Dimethylformamide → HCID 57899362, compound

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}-benzene sulfonamide (prepared as described in example 25, 0.500 g, 0.898 mmol) in N,N-dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 5-amino-2-bromopyridine (0.220 g, 1.24 mmol), cesium carbonate (0.540 g, 1.65 mmol), Pd(dppf)2Cl2 (0.060 g, 0.083 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 4 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-[2-[4-(5-amino-pyridin-2-yl)-phenyl]-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-benzene sulfonamide. 1H NMR (CD3OD, 400 MHz) δ 8.57 (s, 1H), 8.46 (m, 1H), 8.06 (m, 1H), 8.01 (m, 1H), 7.93 (m, 2H), 7.78 (m, 1H), 7.65 (m, 5H), 7.37 (m, 4H); LC-MS calculated for C28H20ClN7O3S (M+H+) 570.1, found 570.0.

Provenance & Evidence