Cesium carbonate → HCID 57899410, 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 (prepared as described in example 26, 0.700 g, 1.13 mmol) in N,N-dimethylformamide (15 mL) is degassed with argon for 0.5 h. Then 2-amino-5-bromopyridine (0.290 g, 1.69 mmol), cesium carbonate (0.740 g, 2.26 mmol), Pd(dppf)2Cl2 (0.040 g, 0.056 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 3 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-(6-amino-pyridin-3-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 8.51 (s, 1H), 8.22 (m, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.55 (m, 6H), 7.37 (m, 2H), 7.34 (m, 2H), 7.32 (d, 1H), 7.10 (d, 1H), 3.0 (s, 3H); LC-MS calculated for C29H22ClN7O3S (M+H+) 584.1, found 583.9.

Provenance & Evidence