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

HRID 1524635

반응식

HRID 1524635 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-252b02afed0d4d6b81afbafac7a02450
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079914B2

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