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

HRID 1524635

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

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, 1H), 8.16 (d, J=1.2 Hz, 1H), 8.81 (d, J=1.6 Hz, 1H).

Aufarbeitung

temperatureThe reaction solution was cooled to RT
washThe mixture was washed with a saturated NaCl solution three times
dry with materialThe organic layer was dried over anhydrous MgSO4
customthe insoluble matter was separated by filtration
concentrationThe filtrate was concentrated
customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-252b02afed0d4d6b81afbafac7a02450
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09079914B2

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