Sodium Hydroxide → 2-(2-Benzyl-4-methyl-6-phenylpyrimidin-5-yl)pentanoic acid

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A solution of methyl 2-(2-benzyl-4-methyl-6-phenylpyrimidin-5-yl)pentanoate (67 mg; 0.17 mmol) in ethanol (1 mL), tetrahydrofuran (1 mL) and 2N sodium hydroxide solution (0.895 mL; 1.789 mmol) was stirred for 40 h at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with water and acidified with a 6N hydrochloric acid solution. The suspension was extracted twice with ethyl acetate and the organic layers were washed with water and dried by filtration over a phase separater filter (PS1). The crude material was purified first by flash chromatography on silica gel using a linear gradient of methanol (1-10%) in dichloromethane and then by preparative thick layer chromatography on silica gel eluting with 10% methanol in dichloromethane to give 25 mg (37%) of the title compound as a colorless oil. ESI/APCI(+): 361 (M+H).

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