Benzyl Chloride → Methyl 4-benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylate

HRID 2241301Notes

Reaction equation

HRID 2241301 reaction equation
[H-].[Li+].[O:3]=[C:4]1[NH:9][CH:8]=[CH:7][N:6]=[C:5]1[C:10]([O:12][CH3:13])=[O:11].Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([N:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]1=[O:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 62714Lithium hydrideHCID 1514283Methyl 3-hydroxypyrazine-2-carboxylate

Product 1

HCID 67348566Methyl 4-benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylateYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

LiH (7.8 mg, 0.980 mmol) was added to the solution of methyl 3-oxo-3,4-dihydropyrazine-2-carboxylate (100 mg, 0.65 mmol) in DMF (3 mL) at 0° C. After 30 minutes stirring, (chloromethyl)benzene (0.15 mL, 1.30 mmol) was added to the reaction mixture at 0° C., and then the reaction was warmed to room temperature. After stirring for 4 hours, the reaction mixture was quenched with ice water, extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated to give the crude material that was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2) to afford 0.102 g (64%) of the desired product.

Workup

  1. stirringAfter stirring for 4 hours
  2. customthe reaction mixture was quenched with ice water
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give the crude material that
  8. customwas purified by silica gel flash column chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-17949065ca0f4eeca22acebe4fa0b116
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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