Sodium Carbonate → 2-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

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Reaction Conditions

Reaction Steps

A suspension of 2-mercapto-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (8.8 g, 40 mmol) in a mixed solvent of dimethylformamide (30 ml) and 1,2-dichloroethane (30 ml) was added to phosphorus oxychloride (11.2 ml, 120 mmol), and the mixture was stirred at 65° C. for 50 min. After the solution was poured into ice-cooled dichloromethane (300 ml), water was added and the mixture was stirred vigorously for 5 min. Aqueous sodium carbonate solution (25.4 g, 240 mmol, in water (100 ml)) was added and the pH was adjusted to 8 with saturated aqueous sodium hydrogencarbonate solution. Aqueous sodium hypochlorite solution (5% in water, 120 ml) was added. After filtration through celite, the organic layer was separated and the aqueous layer was extracted with dichloromethane twice. The organic layers were combined and washed with saturated aqueous sodium hydrogencarbonate solution and dried over sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (eluent; ethyl acetate/hexane=1/1) and wash with diethyl ether to give 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (2.2 g, 62%, 98.7% purity) as a pale-yellow solid.

Provenance & Evidence