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

HRID 390049Notes

Reaction equation

HRID 390049 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
110 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-1cde2d3cecf44ecda66b537a70d27594
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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