Allyl bromide → 6-Methoxy-4-(2-propen-1-yl)pyrido[2,3-b]pyrazin-3(4H)-one

Participants

Reaction Steps

Lithium bromide (514 mg, 5.92 mmol) and subsequently sodium hydride (55%, oily, 258 mg, 5.92 mmol) were added under cooling on ice to a solution of 6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (1.00 g, 5.64 mmol) in N,N-dimethylformamide (30 ml) and the mixture was stirred at room temperature for 1 hour. The reaction solution was cooled on ice again, allyl bromide (0.537 ml, 6.20 mmol) was added thereto and the mixture was stirred for 3 hours while gradually raising the temperature to room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 1.20 g (98%) of the title compound in the form of a yellowish solid.

Provenance & Evidence