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

HRID 1693173Notes

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

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

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

Sources & evidence

ORD record: ord-e44e1d328e314141bd720a98534a7c51
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158620B2

Reaction notes

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