反应详情

N-(5-Hydroxypyrimidin-2-yl)hexanamide (8.18 g, 39 mmol) and triphenylphosphine (20.5 g, 78 mmol) were mixed, and dried under reduced pressure, and then the atmosphere was substituted with argon. These substances were dissolved by heating in anhydrous N,N-dimethylformamide (80 mL), and the solution was cooled to room temperature, and then added with 2-methylthioethanol (5.40 g, 58.6 mmol). The reaction mixture was added with DEAD (2.2 M solution in toluene, 26.6 mL, 58.6 mmol) on an ice bath, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with water (300 mL), and the mixture was stirred for 15 minutes, and then extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, the resulting residue was dissolved in saturated ammonia in methanol (60 mL), and the solution was left at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→hexane:acetone=2:1), the eluate was concentrated under reduced pressure, and the resulting residue was dissolved in chloroform by heating. The crystals obtained by ice cooling of the solution were removed, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from chloroform-hexane to obtain N-{5-[2-(methylthio)ethoxy]pyrimidin-2-yl}hexanamide (6.80 g, 61%) as a pale dark brown solid.

1. customdried under reduced pressure
2. dissolutionThese substances were dissolved
3. temperatureby heating in anhydrous N,N-dimethylformamide (80 mL)
4. stirringthe mixture was stirred for 15 minutes
5. extractionextracted with chloroform
6. washThe organic layer was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. dissolutionthe resulting residue was dissolved in saturated ammonia in methanol (60 mL)
10. waitthe solution was left at room temperature for 1 hour
11. concentrationThe reaction mixture was concentrated under reduced pressure
12. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→hexane:acetone=2:1)
13. concentrationthe eluate was concentrated under reduced pressure
14. dissolutionthe resulting residue was dissolved in chloroform
15. temperatureby heating
16. customThe crystals obtained by ice
17. temperaturecooling of the solution
18. customwere removed
19. concentrationthe filtrate was concentrated under reduced pressure
20. customThe residue was recrystallized from chloroform-hexane