Cesium carbonate → 2-(4-Fluorophenyl)-8-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

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Reaction Conditions

Reaction Steps

Into a flask was added 2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazine (Preparation #K.1; 4.8 g, 21.0 mmol), 4-iodo-2-(methylthio)pyrimidine (Frontier, 9.4 g, 31.7 mmol), Cs2CO3 (10.3 g, 31.7 mmol), PPh3 (2.2 g, 8.4 mmol), and DMF (50 mL). The mixture was degassed under vacuum and back-filled with N2. The mixture was charged with Pd(OAc)2 (0.95 g, 4.2 mmol) and heated at about 100° C. for about 16 h. The mixture was cooled to ambient temperature, diluted with water (200 mL), and extracted with DCM (3×200 mL). The combined organic layers were washed with brine (200 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (0-5% MeOH:DCM) followed by trituration in EtOAc yielded the title compound (4.30 g, 58% yield): LC/MS (Table 1, Method b) Rt=2.2 min; MS m/z: 352.3 (M+H)+.

Provenance & Evidence