Sodium Carbonate → 4-(3,5-Dimethylphenyl)benzofuro[3,2-d]pyrimidine

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Reaction Steps

First, 4.02 g of 4-chlorobenzofuro[3,2-d]pyrimidine, 4.52 g of 3,5-dimethylphenylboronic acid, 3.21 g of sodium carbonate, 0.17 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile were put into a recovery flask equipped with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to microwave irradiation (2.45 GHz, 100 W) for 60 minutes. Further, 0.75 g of 3,5-dimethylphenylboronic acid, 0.53 g of sodium carbonate, and 0.043 g of Pd(PPh3)2Cl2 were added to the mixture, and the reaction container was heated again by 60-minute microwave irradiation (2.45 GHz, 100 W). After that, water was added to this solution and extraction with dichloromethane was carried out. The obtained solution of the extract was washed with water and saturated brine and dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by flash column chromatography using a developing solvent in which the ratio of dichloromethane to ethyl acetate was 10:1, so that Hdmpbfpm, which was the pyrimidine derivative to be produced, was obtained as a white powder in a yield of 74%. Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme of Step 1 is illustrated in (e-1) below.

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