Dimethylformamide → Methyl 4-(cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylate

HRID 1676341Notes

Reaction equation

HRID 1676341 reaction equation
[H-].[Li+].[O:3]=[C:4]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=C[CH:7]=[CH:6][NH:5]1.Br[CH2:15][CH:16]1[CH2:18][CH2:17]1.C[N:20](C=O)C>CCOC(C)=O>[CH:18]1([CH2:17][N:5]2[CH:6]=[CH:7][N:20]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]2=[O:3])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 62714Lithium hydrideHCID 81503BromomethylcyclopropaneHCID 579028Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 67349675Methyl 4-(cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

LiH (7.7 mg, 0.97 mmol) was added to the solution of methyl 2-oxo-1,2-dihydropyridine-3-carboxylate (0.10 g, 0.65 mmol) in DMF (3 mL) at 0° C. After stirring for 30 minutes, (bromomethyl) cyclopropane (0.18 g, 1.30 mmol) was added to the reaction mixture at the temperature, and the reaction was warmed to 50° C. After stirring for 3 days at 50° C., the reaction mixture was diluted with EtOAc, quenched with ice water, extracted with EtOAc, dried over MgSO4, and concentrated. The crude was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2) to afford 87 mg (64%) of the desired product.

Workup

  1. stirringAfter stirring for 3 days at 50° C.
  2. customquenched with ice water
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ea47cddff03044db918ed97dd2b039c8
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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