Tetrabutylammonium Fluoride → tert-Butyl 5,6-dihydroimidazo(1,2-a)pyrazine-7(8H)-carboxylate

HRID 2213053노트

반응식

HRID 2213053 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC[CH2:21][N:22]([CH2:30][C:31]1[N:32]([CH2:36]OCC[Si](C)(C)C)[CH:33]=[CH:34][N:35]=1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>O1CCCC1>[N:35]1[CH:34]=[CH:33][N:32]2[CH2:36][CH2:21][N:22]([C:23]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:29])[CH2:30][C:31]=12

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium Fluoride2회HCID 695594341,1-Dimethylethyl N-(2-Chloroethyl)-N-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-2-ylmethyl)carbamate

생성물 1

HCID 21955306tert-Butyl 5,6-dihydroimidazo(1,2-a)pyrazine-7(8H)-carboxylate수율 35%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 7.1 mL, 7.1 mmol) was added to a solution of 1,1-dimethylethyl N-(2-chloroethyl)-N-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-2-ylmethyl)carbamate (Description 162, 2.52 g, 6.5 mmol) in tetrahydrofuran (50 mL) and the mixture was heated under reflux for 1.5 hours. Further tetrabutylammonium fluoride (1M in tetrahydrofuran, 7.1 mL, 7.1 mmol) was added and the mixture was heated under reflux for 20 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH (97:3), to give the title compound (505 mg, 35%). m/z (ES+) 224 (M+1).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 20 hours
  5. temperatureThe mixture was cooled
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with CH2Cl2/MeOH (97:3)

출처 및 근거

ORD 기록
ord-a962892eda4945aeadf8444726730051
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105507B2

반응 노트

불러오는 중…