Triethylamine → 7-Methyl-6-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbaldehyde

HRID 1158866노트

반응식

HRID 1158866 반응식
Br[C:2](=[CH:5]OC(C)C)[CH:3]=[O:4].[NH2:10][C:11]1[CH2:16][N:15]([CH3:17])[C:14](=[O:18])[CH2:13][N:12]=1.C(N(CC)CC)C>C(#N)C>[CH3:17][N:15]1[C:14](=[O:18])[CH2:13][N:12]2[CH:5]=[C:2]([CH:3]=[O:4])[N:10]=[C:11]2[CH2:16]1.[CH3:17][N:15]1[C:14](=[O:18])[CH2:13][N:12]2[C:2]([CH:3]=[O:4])=[CH:5][N:10]=[C:11]2[CH2:16]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 219413665-Amino-1-methyl-1,6-dihydropyrazin-2(3H)-oneHCID 534166342-Bromo-3-isopropoxy-propenal

생성물 2

HCID 219414037-Methyl-6-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbaldehyde수율 49.1%HCID 219414297-Methyl-6-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-3-carbaldehyde수율 11.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

The solution of 2-bromo-3-isopropoxy-propenal (1.3 g) in dry acetonitrile (60 mL) was added to the solution of 5-amino-1-methyl-3,6-dihydro-1H-pyrazin-2-one (782 mg) in dry acetonitrile (60 mL) at room temperature. The reaction mixture was stirred at room temperature for 20 h, added triethylamine (0.95 mL) and then refluxed for 2 h. The reaction mixture was cooled to room temperature and then evaporated under reduce pressure. The residue was dissolved in chloroform (10 mL) and washed with 50% K2CO3 aqueous solution (10 mL). The aqueous layer was extracted with chloroform. The organic layer was dried (MgSO4) and filtered. The filtrate was evaporated under reduce pressure. The residue was applied to silica gel column chromatography and eluted with CHCl3-MeOH (95:5) to obtain the title compound 7-Methyl-6-oxo-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine-2-carbaldehyde as a pale yellow solid (541 mg, 49.1%) and its regio isomer 7-Methyl-6-oxo-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine-3-carbaldehyde as a pale yellow solid (128 mg, 11.6%).

후처리

  1. temperaturerefluxed for 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customevaporated
  4. dissolutionThe residue was dissolved in chloroform (10 mL)
  5. washwashed with 50% K2CO3 aqueous solution (10 mL)
  6. extractionThe aqueous layer was extracted with chloroform
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. washeluted with CHCl3-MeOH (95:5)

출처 및 근거

ORD 기록
ord-45096445f84e4c429c7eece6b6cad0da
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812014B2

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