반응 #335820

반응 방정식

methyl 4-amino-2-cyclopropylimidazole-5-carboxylate

methyl 4-amino-2-cyclopropylimidazole 5-carboxylate

acetic acid

acetonylacetone

→

title compound

수율 95.6%

Methyl 2-cyclopropyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)imidazole-5-carboxylate

수율 95.6%

용매

ethanol

반응 조건

후처리

1. 1
   온도the mixture refluxed
2. 2
   온도refluxed for 18 hours
3. 3
   기타The solvent was removed under reduced pressure
4. 4
   기타the residue purified by flash chromatography
5. 5
   세척eluting with a gradient of CH2Cl2 to 20% EtOAc in CH2Cl2

실험 절차

A suspension of methyl 4-amino-2-cyclopropylimidazole-5-carboxylate (Example 40, 5.72 g, 0.032 mol) in ethanol (40 mL) was treated with acetic acid (25 mL) and the mixture refluxed to effect solution. To the hot solution was added acetonylacetone (5.41 g, 0.047 mol) and the whole stirred and refluxed for 18 hours. The solvent was removed under reduced pressure and the residue purified by flash chromatography eluting with a gradient of CH2Cl2 to 20% EtOAc in CH2Cl2 to afford 7.93 g of the title compound methyl 2-cyclopropyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)imidazole-5-carboxylate. 1H-NMR (CDCl3) 5.85 (s, 2H), 3.68 (s, 3H), 2.0 (s, 6H), 1.80-2.0 (m, 1H), 1.0-1.18 (m, 4H).

출처