Potassium Carbonate → 2-p-Tolyl-tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione

HRID 2194363ノート

反応式

HRID 2194363 の反応式
[C:1]1(=[O:11])[NH:6][CH2:5][CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH:9]=[C:2]12.[C:12]1([CH3:19])[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.[Cu]I>[C:12]1([CH3:19])[CH:17]=[CH:16][C:15]([N:6]2[CH2:5][CH2:4][N:3]3[C:7](=[O:10])[CH2:8][CH2:9][CH:2]3[C:1]2=[O:11])=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 66867679Tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione

生成物 1

HCID 668659462-p-Tolyl-tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione収率 30%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione (compound of Description 15, 150 mg, 0.97 mmol), p-tolyliodide (424 mg, 1.94 mmol), CuI (62 mg, 0.32 mmol) and K2CO3 (134 mg, 0.98 mmol) in dimethylformamide (6 ml) was refluxed for 2 hours. The solvent was removed under vacuum; the residue was triturated with ethyl acetate and after filtering off the insoluble material, the organic layer was washed with brine, dried (Na2SO4) and evaporated under vacuum. The residue was purified by flash chromatography (DCM/MeOH 95/5 respectively) to give the title compound as a light brown powder (70 mg, 30% yield).

後処理

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue was triturated with ethyl acetate
  4. filtrationafter filtering off the insoluble material
  5. washthe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated under vacuum
  8. customThe residue was purified by flash chromatography (DCM/MeOH 95/5 respectively)

出典と根拠

ORDレコード
ord-e6c497078d504ef3bfe33c703e8a3c11
出典データセット
uspto-grants-2012_12
特許番号
US08334286B2

反応ノート

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