Cesium carbonate → HCID 57899399, compound

Participants

Reaction Conditions

Reaction Steps

A reaction tube is charged with 6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one (32 mg, 0.053 mmol), 2-chloropyrizine (12.1 mg, 0.106 mmol), Cs2CO3 (34.5 mg, 0.106 mmol), Pd2(dba)3 (5.5 mg, 0.005 mmol), 1,3-bis-(2,6-diisopropyl-phenyl)-3H-imidazol-1-ium chloride (4.7 mg, 0.011 mmol) and anhydrous 1,4-dioxane (0.5 mL). The mixture is thoroughly degassed by alternately connecting the flask to vacuum and N2 for three times. The dark red reaction mixture is then heated at 90° C. for 16 h. The reaction mixture is then cooled down to room temperature and treated with H2O (10 mL). EtOAc is used for the extraction (3×3 mL). The combined extracts are concentrated under vacuum and purified by preparative LC/MS to provide the title compound. 1H NMR (CDCl3) δ (ppm) 9.03 (s, 1H), 8.93 (s, 1H), 8.66 (s, 1H), 8.55-8.60 (m, 2H), 8.07 (d, 1H), 7.99 (d, 2H), 7.83 (t, 1H), 7.52 (d, 2H), 7.37 (d, 2H), 7.16 (d, 2H), 3.14 (s, 1H). HPLC-MS calculated C27H17ClN6O (M+H+): 477.1, found: 477.1. HPLC-MS calculated C27H18ClN7O3S (M+H+): 556.1, found: 556.1

Provenance & Evidence