Nitrogen → 2-chloro-4-(3,5-dimethyl-isoxazol-4-yl)-6,7-dihydro-5H-cyclopentapyrimidine

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Reaction Conditions

Reaction Steps

3,5-Dimethylisoxazole boronic acid (0.4 g, 2.8 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.75 g, 4 mmol) in tetrahydrofuran (10 mL). The mixture was flushed with N2 before addition of palladium acetate (0.07 g, 0.28 mmol) and triphenylphosphine (0.14 g, 0.56 mmol). Thereafter, 2M aqueous sodium carbonate solution was added and the mixture was reflushed with N2. The mixture was stirred at a temperature in the range of 20° C. to 50° C. for 8 to 12 hours and then cooled to about 20 to 35° C. The mixture was diluted with water and the organic layer was separated. The aqueous layer was re-extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel) to afford the title compound as a light yellow liquid (0.52 g, 53% yield).

Provenance & Evidence