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

Temperature

-78 °C

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.

1. additionmixed for 30 minutes
2. temperatureWhile maintaining the temperature at −78° C.
3. stirringthe mixture was stirred for 30 minutes
4. temperatureThe temperature was raised to 0° C.
5. stirringthe reaction solution was stirred for 1 hour
6. washwashed with water
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. customthe solvent was removed under reduced pressure

ORD record

ord-c58e5549790e4c0ba7043c213edbb547

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952010B2