Allyl bromide → HCID 21713978, compound

HRID 650243Notes

Reaction equation

HRID 650243 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([OH:12])=[N:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C)C=O>[CH2:23]([N:10]1[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][N:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]1=[O:12])[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178470228HCID 178470228, compound

Product 1

HCID 21713978HCID 21713978, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Ethyloxycarbonyl-3-hydroxy-5-phenylpyrazine (214.4 mg, 0.88 mmol) was dissolved in dimethylformamide (2.1 ml), and sodium hydride (60% in oil, 42.1 g, 1.05 mmol) was added to it under cooling on ice and stirred for 30 minutes. After allyl bromide (0.11 ml, 1.32 mmol was added, the mixture was stirred at room temperature for 1 hour and then at 80° C. for 1 hour. The reaction solution was left to be cooled to room temperature, thereafter the reaction was terminated by adding distilled water, and the product was extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the drying agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) whereby the title compound was obtained (24 mg, 9.6% yield).

Workup

  1. temperatureunder cooling on ice
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. waitat 80° C. for 1 hour
  4. waitThe reaction solution was left
  5. customthe reaction was terminated
  6. additionby adding
  7. distillationdistilled water
  8. extractionthe product was extracted twice with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. customthe drying agent was removed by filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) whereby the title compound
  13. customwas obtained (24 mg, 9.6% yield)

Sources & evidence

ORD record
ord-bc0fd2d5e3834c649461919d3dbeefeb
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

Loading…