반응 #75779

반응 방정식

trimethyl orthovalerate

1,1-Dimethylethyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethyl}carbamate

trimethyl orthovalerate

toluene

→

1,1-dimethylethyl N-[2-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate

수율 47.4%

용매

Xylene

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도at reflux for 2 hours
3. 3
   온도the reaction mixture was heated
4. 4
   온도at reflux overnight
5. 5
   workup.DISTILLATIONthe toluene was distilled off
6. 6
   온도The reaction was heated
7. 7
   온도at reflux for an additional 8 hours
8. 8
   workup.DISTILLATIONThe bulk of the xylene was distilled off
9. 9
   기타leaving a volume of about 5 mL
10. 10
    온도to cool
11. 11
    기타The resulting precipitate was isolated by filtration
12. 12
    세척washed with heptane
13. 13
    기타dried

실험 절차

1,1-Dimethylethyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethyl}carbamate 0.6 g, 2 mmol), trimethyl orthovalerate (0.35 g, 2.1 mmol), and toluene (25 mL) were combined and heated at reflux for 2 hours. Additional trimethyl orthovalerate (1 eq.) was added and the reaction mixture was heated at reflux overnight. Xylene was added and the toluene was distilled off. The reaction was heated at reflux for an additional 8 hours. The bulk of the xylene was distilled off leaving a volume of about 5 mL. The reaction mixture was allowed to cool. The resulting precipitate was isolated by filtration, washed with heptane and dried to provide 0.35 g of 1,1-dimethylethyl N-[2-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate as an ivory powder, m.p. 198-199° C. Analysis: Calculated for C20H27N5O2: %C, 65.01; %H, 7.36; %N, 18.95. Found: %C, 64.75; %N, 7.57; %N, 19.09.

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