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

HRID 1158866ノート

反応式

HRID 1158866 の反応式
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

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-45096445f84e4c429c7eece6b6cad0da
出典データセット
uspto-grants-2010_10
特許番号
US07812014B2

反応ノート

読み込み中…