Methanol → N-(5-Hydroxypyrimidin-2-YL)hexanamide

N-(5-Methoxypyrimidin-2-yl)hexanamide (17.3 g, 77 mmol) was suspended in 1,2-dichloroethane (170 mL), the suspension was added with boron tribromide (20.5 mL, 216 mmol), and the mixture was refluxed by heating for 30 minutes. The reaction mixture was inactivated with methanol (170 mL) under ice cooling. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with saturated ammonia in methanol (85 mL) under ice cooling, and the mixture was homogenized. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with water, and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, and the resulting residue was isolated and purified by silica gel column chromatography (hexane:acetone=2:1) to obtain N-(5-hydroxypyrimidin-2-yl)hexanamide (9.36 g, 59%) as a pale yellow solid.

1. temperaturethe mixture was refluxed
2. temperatureby heating for 30 minutes
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. additionthe resulting residue was added with saturated ammonia in methanol (85 mL) under ice cooling
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. additionthe resulting residue was added with water
7. extractionextracted with chloroform
8. washThe organic layer was washed with saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure
11. customthe resulting residue was isolated
12. custompurified by silica gel column chromatography (hexane:acetone=2:1)

ORD record

ord-05433868c506467f9f04b721ebbea220

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659271B2