Sodium Hydroxide → HCID 68689034, compound

Participants

Reaction Steps

15 g of ethyl ethynyl ether (40% hexane solution) was dissolved in 50 mL of tetrahydrofuran, and 29 mL of a borane-tetrahydrofuran complex (1M tetrahydrofuran solution) was added to the solution at 0° C. After stirring at room temperature for 4 hours and a half, 150 mL of a tetrahydrofuran solution containing 4.0 g of the 4-chloro-6-methyl-2-(methylthio)pyrimidine [42-1], 35 mL of a 3 N aqueous solution of sodium hydroxide, 0.46 g of triphenylphosphine and 0.34 g of palladium acetate were added thereto. The obtained reaction solution was stirred at room temperature for 16 hours, and then 200 mL of water was added to the reaction solution. The reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated brine. After drying the organic layer over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and 4.9 g of 4-[(E)-2-ethoxyvinyl]-6-methyl-2-(methylthio)pyrimidine [42-2] was obtained as a brown oily product.

Provenance & Evidence