N'-(1-benzyl-4-methyl-5-nitro-6-oxopyrimidin-2-yl)-N,N-dimethylmethanimidamide → N'-[1-benzyl-4-[(E)-2-(dimethylamino)ethenyl]-5-nitro-6-oxopyrimidin-2-yl]-N,N-dimethylmethanimidamide
Reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([N+:15]([O-:17])=[O:16])=[C:11]([CH3:18])[N:10]=[C:9]1/[N:19]=[CH:20]/[N:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C=O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([N+:15]([O-:17])=[O:16])=[C:11](/[CH:18]=[CH:1]/[N:8]([CH3:13])[CH3:9])[N:10]=[C:9]1/[N:19]=[CH:20]/[N:21]([CH3:22])[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
3
Conditions
- Temperature
- 65 °C
Procedure
To a solution of (E)-N′(1-benzyl-4-methyl-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)-N,N-dimethylformimidamide (64.7 g, 0.2 mol) in DMF (254 mL) was added DMF-dimethylacetal (54.5 mL, 0.41 mol). The reaction mixture was stirred for 3 h at 65° C., cooled, and the solvent was removed under reduced pressure. The residue was triturated with ethanol, and the solid was collected by vacuum filtration (69.2 g, 91%) and used in the next step without further purification.