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

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Reaction Conditions

Reaction Steps

Pd(OAc)2 (0.233 g, 1 mmol) was added to a degassed mixture of 2-(4-fluorophenyl)-8-isopropoxyimidazo[1,2-a]pyrazine (1.43 g, 5.2 mmol), 4-iodo-2-(methylthio)pyrimidine (Frontier, 1.96 g, 7.8 mmol), Cs2CO3 (2.57 g, 7.8 mmol) and PPh3 (0.54 g, 2 mmol) in DMF (6 mL). The resulting reaction mixture was heated at about 100° C. for about 4 h, cooled to ambient temperature, and partitioned between EtOAc and brine. The organic layer was separated, dried over MgSO4, filtered, and evaporated. The crude material was purified by silica gel chromatography using heptane/EtOAc (gradient, 100%/0% to 50%/50%) to afford 1.05 g (51%) of the title compound: LC/MS (Table 1, Method g) Rt=3.45 min; MS m/z: 396.2 (M+H)+.

Provenance & Evidence