N-bromobutanimide → 5-(2-bromothiophen-3-yl)-3,6-dimethyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione

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Reaction Steps

To a solution of 3,6-dimethyl-5-(thiophen-3-yl)-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference example 199) (30.7 mg) in acetic acid (1.5 ml) was added N-bromosuccinimide (20.2 mg) and the resulting mixture was stirred at room temperature for three hours. To the reaction mixture were added an aqueous saturated sodium hydrogen carbonate solution (10 ml) and an aqueous saturated sodium thiosulfate solution (10 ml), and the resulting mixture was extracted with ethyl acetate (10 ml×2). The organic layer was washed with saturated saline (20 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 5-(2-bromothiophen-3-yl)-3,6-dimethyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (17.4 mg).

Provenance & Evidence