[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.O1CCCC1.C(O)C>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1To a solution of methyl 2-(3-fluorophenyl)pyrimidine-5-carboxylate (45 g, 0.19 ml) in a 1:1 mixture of tetrahydrofuran and ethanol (120 mL) was added Li(OH).H2O (12.2 g, 0.29 mol) dissolved in water (120 mL) and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated under reduced pressure, dissolved in water (500 mL), acidified with 1N aqueous HCl and filtered. The residue was washed with water (100 mL×3) and dried to give 37 g (yield 89.5%) of 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid. 1H NMR (DMSO-d6) 7.49 (m, 1H) 7.67 (m, 1H) 8.18 (m, 1H) 8.34 (m, 1H) 9.34 (s, 2H). LRMS (ES+) M+H 219.
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