Dimethylformamide → 4-[(E)-2-(dimethylamino)ethenyl]-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile
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]=1Participants
3
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