Acetic Acid → Ethyl imidazo(1,2-c)pyrimidine-7-carboxylate

HRID 25166

반응식

HRID 25166 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[N+:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[C-:9].C1CCN2C(=NCCC2)CC1.CC(O)=O>O1CCOCC1>[N:3]1[CH:4]=[CH:5][N:1]2[C:2]=1[CH:6]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[CH:9]2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetate

생성물 1

HCID 22566015Ethyl imidazo(1,2-c)pyrimidine-7-carboxylate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a suspension of imidazole-2-carboxaldehyde (2.3 g, 23.4 mmol) in 50 mL dioxane is added to ethyl isocyanoacetate (2.9 g, 25.8 mmol) and DBU (3.9 g, 25.8 mmol). After stirring at RT for 5 days, the reaction is neutralized with 10% AcOH. The solvent is removed in vacuo. The residue is taken up in EtOAc/H2O, the aqueous layer is extracted with CHCl3, dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40M, eluting with 5% MeOH/EtOAc). Ethyl imidazo[1,2-c]pyrimidine-7-carboxylate is obtained (1.4 g, 32%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ9.14, 8.43, 7.88, 7.81, 4.54-4.48, 1.49-1.44.

후처리

  1. customThe solvent is removed in vacuo
  2. extractionthe aqueous layer is extracted with CHCl3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography (Biotage 40M, eluting with 5% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-75566e8a19114934948489b12d480eb1
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858613B2

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