Dimethyl Sulfoxide → 2-(methoxymethoxy)-3-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)propanal

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.022 ml, 0.260 mmol) was dissolved in dichloromethane (1 ml), a solution of dimethyl sulfoxide (0.037 ml, 0.521 mmol) in dichloromethane (0.5 ml) was added to the solution at −78° C. and mixed for 30 minutes. While maintaining at −78° C., a solution of 4-[3-hydroxy-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (64 mg, 0.217 mmol) in dichloromethane (3 ml) was added to the reaction solution and the mixture was stirred for 1 hour. While maintaining the temperature at −78° C., triethylamine (0.181 ml, 1.302 mmol) was added to the reaction solution and the mixture was stirred for 30 minutes. The temperature was raised to 0° C., the reaction solution was stirred for 1 hour, then diluted with dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 67 mg (quantitative) of the title compound in the form of a yellow-orange oily product. The product was used as such for next reaction without purification.

Provenance & Evidence