반응 #2453885

반응 방정식

pyridine hydrochloride

trimethyl orthobutyrate

ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate

→

ethyl 4-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoate

수율 150.2%

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도at reflux for 1.5 hours
3. 3
   농축concentrated under reduced pressure
4. 4
   기타The residue was partitioned between chloroform (300 mL) and saturated aqueous sodium bicarbonate (75 mL)
5. 5
   추출The aqueous layer was extracted with chloroform (2×100 mL)
6. 6
   세척the combined organic fractions were washed with saturated aqueous sodium bicarbonate (2×75 mL)
7. 7
   건조dried over magnesium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The resulting solid was triturated with ethyl acetate
11. 11
    기타isolated by filtration

실험 절차

For Examples 40 and 41, pyridine hydrochloride (1.34 g, 11.6 mmol) and trimethyl orthobutyrate (5.42 mL, 34.1 mmol) were sequentially added with stirring to a solution of ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate (9.1 g, 31 mmol) in toluene (310 mL) under a nitrogen atmosphere. The reaction was heated at reflux for 1.5 hours, allowed to cool to ambient temperature overnight, and concentrated under reduced pressure. The residue was partitioned between chloroform (300 mL) and saturated aqueous sodium bicarbonate (75 mL). The aqueous layer was extracted with chloroform (2×100 mL), and the combined organic fractions were washed with saturated aqueous sodium bicarbonate (2×75 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was triturated with ethyl acetate and isolated by filtration to provide 6.0 g of ethyl 4-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoate as a white solid.

출처