Water → 4,6-Bis-(4-methoxy-phenyl)-2-methyl-pyrimidine

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Reaction Steps

The 4,6-dichloro-2-methylpyrimidine 22 (0.10 g, 0.6 mmol) is dissolved in dioxane (1 mL). 4-Methoxy-phenylboronic acid (0.32 g, 2.1 mmol) is added, followed by water (0.01 mL), ethanol (0.01 mL), potassium carbonate (0.40 g, 2.9 mmol), and tetrakistriphenyl-phosphino)palladium (0.13 g, 0.11 mmol). The mixture is stirred under nitrogen and subjected to microwave (170° C. for 5 min). The resulting orange suspension is filtered, the solids are washed with more dioxane, and the resulting solution is concentrated and purified by silica gel chromatography (5% to 25% ethyl acetate in hexanes) to yield the 4,6-bis-(4-methoxy-phenyl)-2-methyl-pyrimidine 23 as an oil. 1H-NMR (400 MHz, CDCl3) δ=8.03 (d, J=8.8 Hz, 2H), 7.70 (s, 1H), 6.95 (d, J=8.8 Hz, 2H), 3.82 (s, 6H), 2.77 (s, 3H). MS calculated for C19H19N2O2 (M+H+) 306.15, found 306.9.

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