Dimethylformamide → HCID 16755793, 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, 0.82 mmol) in N,N-dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.250 g, 1.24 mmol), cesium carbonate (0.530 g, 1.65 mmol), Pd(dppf)2Cl2 (0.06 g, 0.08 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 50° C. for 12 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 column chromatography over silica gel (60-120 mesh) to afford 3-[1-(4-chloro-phenyl)-6-oxo-2-(4-pyrazin-2-yl-phenyl)-1,6-dihydro-purin-9-yl]-benzene sulfonamide. 1H NMR (DMSO-d6, 400 MHz) δ 9.24 (m, 1H), 8.69 (m, 1H), 8.63 (m, 1H), 8.30 (m, 1H), 8.02-8.08 (m, 2H), 7.94 (m, 1H), 7.82 (m, 1H), 7.43-7.58 (m, 8H), 7.15 (br, 2H); LC-MS calculated for C27H18ClN7O3S (M+H+) 556.1, found 555.9.

Provenance & Evidence