Dimethylformamide → t-butyl 5-((E)-2-dimethylaminovinyl)pyrazine-2-carboxylate

HRID 1842093Notes

Reaction equation

HRID 1842093 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1.[CH3:15][N:16]([CH3:19])[CH:17]=O.COC(OC)N(C)C>C(OCC)(=O)C>[CH3:15][N:16]([CH3:19])/[CH:17]=[CH:1]/[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 57475683t-Butyl 5-methylpyrazine-2-carboxylate

Product 1

HCID 57475684t-butyl 5-((E)-2-dimethylaminovinyl)pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of t-butyl 5-methylpyrazine-2-carboxylate (1.35 g), N,N-dimethylformamide (25 mL) and N,N-dimethylformamide dimethylacetal (25 mL) was stirred at 130° C. for five hours. The reaction solution was cooled to room temperature and diluted with ethyl acetate. The mixture was washed with a saturated sodium chloride solution three times. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain the title compound (648 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washThe mixture was washed with a saturated sodium chloride solution three times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe insoluble matter was separated by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6b3523e3687c4a8ab95fe58d326aa63a
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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