Cesium carbonate → HCID 57897833, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-chloro-phenyl)-9-phenyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,9-dihydro-purin-6-one (180 mg, 0.34 mmol) and 2-amino-5-bromopyridine (89 mg, 0.51 mmol) in anhydrous DMF (3 mL) was treated sequentially with Cs2CO3 (224 mg, 0.69 mmol) and Pd(dppf)2Cl2 (14 mg, 0.017 mmol). The reaction mixture was degassed with N2 and heated at 100° C. for 24 h. The reaction was cooled to room temperature, diluted with H2O, and extracted with EtOAc. The combined organics were dried (MgSO4), filtered, and concentrated. The crude material was purified by flash column chromatography (silica, 30% EtOAc/CH2Cl2) to provide the title compound 2-[4-(6-amino-pyridin-3-yl)-phenyl]-1-(4-chloro-phenyl)-9-phenyl-1,9-dihydro-purin-6-one as a white solid. 1H NMR (CDCl3) δ (ppm) 8.19 (s, 1H), 7.95 (m, 2H), 7.72 (d, 2H), 7.61 (apparent t, 2H), 7.52 (apparent t, 1H), 7.42 (d, 2H), 7.35 (m, 4H), 7.17 (d, 2H), 6.95 (d, 1H); HPLC-MS calculated for C28H19ClN6O (M+H+): 491.1. Found: 491.1.

Provenance & Evidence