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

HRID 1429630

Reaction equation

HRID 1429630 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]([CH:18]=O)[CH3:17].COC(OC)N(C)C>CCOC(C)=O>[CH3:15][N:16]([CH3:18])/[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), DMF (25 mL) and N,N-dimethylformamide dimethylacetal (25 mL) was stirred at 130° C. for 5 h. The reaction solution was cooled to RT and diluted with EtOAc. The mixture was washed with a saturated NaCl solution three times. The organic layer was dried over anhydrous MgSO4, 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). 1H-NMR (CDCl3) δ (ppm): 1.63 (s, 9H), 3.00 (s, 6H), 5.16 (d, J=12.8 Hz, 1H), 7.72 (d, J=12.8 Hz, 1 H), 8.16 (d, J=1.2 Hz, 1H), 8.81 (d, J=1.6 Hz, 1H).

Workup

  1. temperatureThe reaction solution was cooled to RT
  2. washThe mixture was washed with a saturated NaCl solution three times
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  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-11f0504771a747e79eb33b206549c666
Source dataset
uspto-grants-2015_01
Patent number
US08940734B2

Linked notes

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