Cesium carbonate → HCID 24781188, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(4-chloro-phenyl)-1-(3-methanesulfonyl-phenyl)-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]-pyrimidin-4-one (prepared as described in example 51, 0.500 g, 0.829 mmol) in N,N-dimethylformamide (30 mL) is degassed with argon for 0.5 h. Then 2-bromopyrimidine (0.197 g, 1.24 mmol), cesium carbonate (0.540 g, 1.66 mmol), Pd(dppf)2Cl2 (0.06 g, 0.082 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is heated to 100° C. for 2 h. The reaction mixture is 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 5-(4-chloro-phenyl)-1-(3-methanesulfonyl-phenyl)-6-(4-pyrimidin-2-yl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one. 1H NMR (CDCl3 400 MHz) δ 8.89 (m, 3H), 8.60 (m, 1H), 8.46 (m, 2H), 8.38 (s, 1H), 7.92-7.95 (m, 1H), 7.74 (m, 1H), 7.54 (m, 2H), 7.33-7.36 (m, 3H), 7.13-7.17 (m, 2H); LC-MS calculated for C28H19ClN6O3S (M+H+) 555.1, found 554.9.

Provenance & Evidence