Acetonitrile → 4-Chloro-6-phenylpyrimidine

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Reaction Steps

First, 5.0 g of 4,6-dichloropyrimidine, 4.9 g of phenylboronic acid, 7.1 g of sodium carbonate, 0.34 g of bis(triphenylphosphine)palladium(II) dichloride, namely PdCl2(PPh3)2, 20 mL of acetonitrile, and 20 mL of water were put into a 100-mL round-bottom flask equipped with a reflux pipe, and the air in the flask was replaced with argon. Then, heating was performed by irradiation with microwaves (2.45 GHz, 100 W) for 1 hour. An organic layer was extracted from the obtained mixture with the use of dichloromethane and was washed with water and saturated brine. Magnesium sulfate was added and gravity filtration was performed. The solvent in the obtained filtrate was distilled off, and the given residue was purified by flash column chromatography using dichloromethane as a developing solvent, whereby 1.6 g of the objective substance was obtained (yield: 23%, a pale yellow solid). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme of Step 1 is shown in (a-1) below.

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