Pyridine → 2-(4-(2-Hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid

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A solution of methyl 2-(4-(2-hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.040 g; 0.099 mmol) and lithium iodide (0.066 g; 0.494 mmol) in pyridine (0.5 mL) was irradiated at 170° C. in a microwave sealed tube for 3 h. The solvent was removed under reduced pressure, the residue was dissolved in water and the pH adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N. The suspension was extracted twice with ethyl acetate and the combined organic layers were concentrated under reduced pressure. The residue was again suspended in water, basified with a solution of sodium hydroxide 5N and washed with a mixture of heptane and ethyl acetate (1:1). The pH of the aqueous solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N, extracted twice with ethyl acetate and the combined organic layers were dried over magnesium sulphate and concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 1) furnished 0.008 g (21%) of 2-(4-(2-hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid and 0.002 g (5%) of 2-(4-(2-methoxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid.

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