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

5-Hydroxypyrimidin-2-amine (40 g, 360 mmol) was dissolved in pyridine (200 mL), the solution was added with hexanoyl chloride (121 g, 899 mmol), and the mixture was stirred at room temperature for 0.5 hour. The reaction mixture was added with methanol (100 mL), the mixture was concentrated under reduced pressure, and the resulting residue was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, and the resulting residue was dissolved in methanol (200 mL). The solution was added with saturated ammonia solution in methanol (250 mL) under ice cooling and stirring, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone=2:1) to obtain N-(5-hydroxypyrimidin-2-yl)hexanamide (39.5 g, 52%) as colorless solid.

1. concentrationthe mixture was concentrated under reduced pressure
2. additionthe resulting residue was diluted with water
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. dissolutionthe resulting residue was dissolved in methanol (200 mL)
8. additionThe solution was added with saturated ammonia solution in methanol (250 mL) under ice cooling
9. stirringstirring
10. stirringthe mixture was stirred overnight at room temperature
11. concentrationThe reaction mixture was concentrated under reduced pressure
12. customthe resulting residue was purified by silica gel column chromatography (hexane:acetone=2:1)

ORD record

ord-75d673a46c844695b472030c3930e715

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012989B2