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

HRID 2194363Notes

Reaction equation

HRID 2194363 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e6c497078d504ef3bfe33c703e8a3c11
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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