Potassium Carbonate → 2,5-Difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene
Reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][N:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17](=[O:24])[NH:16][C:15]1=[O:25].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N:16]2[C:17](=[O:24])[CH:18]=[C:19]([C:20]([F:22])([F:23])[F:21])[N:14]([CH3:13])[C:15]2=[O:25])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
1.77 g of 2,4,5-trifluoronitrobenzene and 1.94 g of 3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine were dissolved in 10 ml of dimethyl sulfoxide, and 1.52 g of anhydrous potassium carbonate was added to this at room temperature, then, the mixture was stirred for 1 hour at 80° C. The reaction solution was allowed to cool to room temperature, then, the reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.51 g of 2,5 difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene.
Workup
- temperatureto cool to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated saline
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1294542146784e74bd5271fc17b79bb0
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06667413B2
Reaction notes
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