反应详情

A solution of [4-amino-7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate (34.0 g, 0.0782 mol) in methanol (150 mL) was heated at reflux, and a solution of aqueous sodium hydroxide (50 mL of 1.7 M) was added, over a period of five minutes. A white precipitate formed, and the reaction was heated at reflux for one hour. The reaction mixture was allowed to cool to room temperature and stirred for about three hours. The precipitate was isolated by filtration, washed with deionized water and methanol, and then dried under vacuum at 50° C. to provide 24.9 g of the crude product. The crude product (6.0 g) was recrystallized from a mixture of 2-propanol:acetic acid 9:1 (470 mL); the hot solution was treated with activated charcoal and filtered through a layer of CELITE filter aid. The crystals were isolated by filtration, washed with a small volume of 2-propanol:acetic acid, and dried under vacuum at 50° C. The product was stirred with aqueous sodium hydroxide (200 mL of 0.15 M) for three hours, isolated by filtration, washed with deionized water, stirred with methanol (100 mL) for one hour, isolated by filtration, washed with methanol, and dried under vacuum at 60° C. Finally, the product (4.5 g) was recrystallized from DMF, isolated by filtration, and dried under vacuum to provide 1-[4-amino-7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as a white solid, mp 284.5-285.5° C.

1. temperatureat reflux
2. customA white precipitate formed
3. temperaturethe reaction was heated
4. temperatureat reflux for one hour
5. customThe precipitate was isolated by filtration
6. washwashed with deionized water and methanol
7. customdried under vacuum at 50° C.
8. customto provide 24.9 g of the crude product
9. customThe crude product (6.0 g) was recrystallized from a mixture of 2-propanol:acetic acid 9:1 (470 mL)
10. additionthe hot solution was treated with activated charcoal
11. filtrationfiltered through a layer of CELITE
12. filtrationfilter aid
13. customThe crystals were isolated by filtration
14. washwashed with a small volume of 2-propanol
15. dry with materialacetic acid, and dried under vacuum at 50° C
16. stirringThe product was stirred with aqueous sodium hydroxide (200 mL of 0.15 M) for three hours
17. customisolated by filtration
18. washwashed with deionized water
19. stirringstirred with methanol (100 mL) for one hour
20. customisolated by filtration
21. washwashed with methanol
22. customdried under vacuum at 60° C
23. customFinally, the product (4.5 g) was recrystallized from DMF
24. customisolated by filtration
25. customdried under vacuum