Cesium carbonate → HCID 136248837, compound

Participants

Reaction Steps

To a suspension of 2-(6-bromopyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (0.193 g, 0.533 mmol) in dioxane (3 mL) was added palladium(II)acetate (0.012 g, 0.053 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.0332 g, 0.053 mmol) and cesium carbonate (0.261 g, 0.800 mmol) under nitrogen. The reaction mixture was refluxed under nitrogen for 6.5 h. After that time the reaction was cooled to rt, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 95:5 dichloromethane/methanol and trace amount of ammonium hydroxide) followed by trituration with diethyl ether to give 2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (0.043 g, 20%) as a light yellow solid: mp 175-177° C.; 1H NMR (400 MHz, DMSO-d) δ 11.05 (br s, 1H), 7.65-7.79 (m, 2H), 7.06 (d, J=8.20 Hz, 1H), 6.78 (s, 1H), 6.58 (s, 1H), 4.48 (br s, 1H), 3.91 (s, 3H), 3.86 (s, 3H), 3.64 (br s, 4H), 3.55 (br s, 2H), 2.54 (br s, 4H), 2.45 (t, 2H); ESI MS m/z 412 [M+H]+.

Provenance & Evidence