[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.COB([C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1)O.[Cl-].[Li+].[C:25](=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.COCCOC>[CH3:25][O:22][C:20](=[O:21])[C:17]1[CH:16]=[CH:15][C:14]([C:6]2[C:5]([Cl:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[CH:19][CH:18]=1
In a flask was added 2,4,5-trichloro-pyrimidine (1.3 equivalents, 2.66 g, 14.6 mmol), the commercially available 4-carboxyphenyl boronic acid methyl ester (1.0 equivalent, 2.02 g, 11.2 mmol), tetrakis triphenylphosphine palladium (0.1 equivalent, 1.3 g, 1.12 mmol), lithium chloride (3.0 equivalents, 1.4 g, 33.6 mmol), sodium carbonate (2N, 5 mL) and 1,2-dimethoxyethane (20 mL). The resulting mixture was heat at 80° C. for 24 hours then dissolved in ethyl acetate, washed with hydrochloric acid (1N), brine and dried over sodium sulfate. The crude product was purified by chromatography on silica (ethyl acetate, 10% in hexane) to afford 1.21 g of 4-(2,5-dichloro-pyrimidin-4-yl)-benzoic acid methyl ester as a white solid. The structure was confirmed by 1H NMR.
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