Water → methyl (E)-3-(2-methoxy-5-pyrimidinyl)acrylate

Participants

Reaction Conditions

Reaction Steps

2-Methoxy-5-iodopyrimidine (1.736 g, 7.36 mmol) was dissolved in 36 ml of N,N-dimethylformamide, and 99 mg of palladium acetate, 2.54 g (18.4 mmol) of potassium carbonate, 2.05 g (7.36 mmol) of tetrabutylammonium chloride and 3.168 g (36.8 mmol) of methyl acrylate were added thereto. The mixture was stirred in an argon atmosphere at 80° C. for 1 hour. Water was added to the reaction mixture, and the solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained crude product was purified by silica-gel column chromatography (250 ml of silica gel, hexane:ethyl acetate=2:1 to 1:1) to give 1.26 g (6.49 mmol) of methyl (E)-3-(2-methoxy-5-pyrimidinyl)acrylate (yield: 88%).

Provenance & Evidence