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

HRID 1676357Notes

Reaction equation

HRID 1676357 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 4 hours stirring, 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. 1H-NMR (400 MHz, CDCl3) δ 7.38 (m, 6H), 7.29 (d, 1H), 5.14 (s, 2H), 3.98 (s, 3H).

Workup

  1. stirringAfter 4 hours stirring
  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-cd58a96de237414f9ca7a8fa7094678c
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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