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

HRID 2241244Notes

Reaction equation

HRID 2241244 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].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.CCOC(C)=O>[CH2:14]([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:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

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

Product 1

HCID 67348566Methyl 4-benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

LiH was added to the solution of methyl 3-oxo-3,4-dihydropyrazine-2-carboxylate (0.10 g, 0.65 mmol) in DMF (3 mL) at 0° C. After stirring for 30 minutes, benzyl chloride (0.15 mL, 1.30 mmol) was added to the reaction mixture at the temperature, and the reaction was warmed to room temperature. After stirring for 3 days, the reaction mixture was diluted with EtOAc, quenched with ice water, extracted with EtOAc, dried over MgSO4, and concentrated to give the desired product, which was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2, 0.102 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.35-7.40 (m, 6H), 7.29 (d, 1H), 5.14 (s, 2H), 3.99 (s, 3H).

Workup

  1. stirringAfter stirring for 3 days
  2. customquenched with ice water
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e6927688158456b874ec9aa6e516599
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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