반응 #1976503

반응 방정식

6-methoxypyridazin-3-amine

methyl 2-amino-5-ethylthiophene-3-carboxylate

triphosgene

triethylamine

→

title compound

수율 62.7%

6-ethyl-3-(6-methoxypyridazin-3-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

수율 62.7%

용매

methylene chloride

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was further stirred at room temperature for 1 hr
2. 2
   세척The reaction mixture was washed with water and saturated brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타The solvent was evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONThe obtained residue was dissolved in methanol (50 mL)
6. 6
   workup.ADDITIONsodium methoxide (3 g) was added
7. 7
   workup.STIRRINGthe mixture was stirred at 60° C. for 2 hr
8. 8
   여과was filtered off
9. 9
   기타the solvent was evaporated under reduced pressure
10. 10
    기타The obtained residue was purified by silica gel column chromatography

실험 절차

To a solution (80 mL) of methyl 2-amino-5-ethylthiophene-3-carboxylate (1 g) in methylene chloride were added triphosgene (0.7 g) and triethylamine (1.19 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 6-methoxypyridazin-3-amine (2 g), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (50 mL), sodium methoxide (3 g) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was neutralized with hydrochloric acid (10% methanol solution), insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.45 g, 27%).

출처