Cesium carbonate → HCID 57899404, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(3-{1-(4-chloro-phenyl)-6-oxo-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,6-dihydro-purin-9-yl}-phenyl)-methane sulfonamide (10, 0.35 g, 0.57 mmol) in N,N-dimethylformamide (15 mL) is degassed with argon for 0.5 h. Then 5-amino-2-bromopyridine (0.147 g, 0.850 mmol), cesium carbonate (0.360 g, 1.13 mmol), Pd(dppf)2Cl2 (0.020 g, 0.028 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 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 preparative HPLC to afford N-{3-[2-[4-(5-amino-pyridin-2-yl)-phenyl]-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-phenyl}-methane sulfonamide, as a yellow solid. 1H NMR (CD3OD, 400 MHz) δ 8.53 (s, 1H), 7.95 (m, 3H), 7.69 (d, 5H), 7.55 (m, 2H), 7.38 (m, 4H), 7.25 (m, 1H), 3.01 (s, 3H); LC-MS calculated for C29H22ClN7O3S (M+H+) 584.1, found 584.1.

Provenance & Evidence