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Dimethylformamide → 4-[(E)-2-(dimethylamino)ethenyl]-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile

HRID 390049
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HRID 390049 반응식
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)[N:5]=[C:4]([S:18][CH3:19])[N:3]=1.[CH3:20][N:21]([CH:23]=O)[CH3:22]>>[CH3:20][N:21]([CH3:23])/[CH:22]=[CH:1]/[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)[N:5]=[C:4]([S:18][CH3:19])[N:3]=1
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참가 물질

3

반응물 2

HCID 6228DimethylformamideHCID 582963344-Methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile

생성물 1

HCID 582963134-[(E)-2-(dimethylamino)ethenyl]-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile

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온도
110 °C

실험 절차

To a solution of 4-methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile (1.32 g, 4.89 mmol) in DMF (8 mL) was added DMF dimethyl acetyl (1.16 g, 9.75 mmol), and the reaction mixture was stirred at 110° C. for 1.5 h. The mixture was concentrated and the residue was dissolved into EtOAc (30 mL). The solution was washed with water and organic layer was collected. The aqueous layer was extracted with EtOAc (2×). The combined extract was dried over Na2SO4, filtered, and concentrated to give the crude enamine product (1.47 g). MS: M(C17H19N5S)=325.44, (M+1)+=326.1

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved into EtOAc (30 mL)
  3. washThe solution was washed with water and organic layer
  4. customwas collected
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. extractionThe combined extract
  7. dry with materialwas dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1cde2d3cecf44ecda66b537a70d27594
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08383635B2

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