Water → 1-(4-Chlorobutyl)-4-(trifluoromethyl)pyrimidin-2(1H)-one
Reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].O>CN(C)C=O>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][N:3]1[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:9])[F:10])=[N:7][C:2]1=[O:1]Participants
6
Procedure
4.6 g (28.3 mmol) of 2-hydroxy-4-trifluoromethylpyrimidine were stirred in 60 ml of N,N-dimethylformamide (DMF) and 3.9 g (28.3 mmol) of K2CO3 at room temperature for 1 hour. Then 4.9 g (28.3 mmol) of 1-bromo-4-chlorobutane were added dropwise, and the reaction mixture was stirred at room temperature for 6 hours. Water was then added to the reaction mixture, and the aqueous mixture was extracted with diethyl ether. The aqueous phase was made alkaline by adding NaOH, and the aqueous phase was extracted with methylene chloride. The organic phase was then dried, the desiccant was removed by filtration, and the solvent was evaporated to dryness in vacuo; yield: 1.7 g.
Workup
- extractionthe aqueous mixture was extracted with diethyl ether
- additionby adding NaOH
- extractionthe aqueous phase was extracted with methylene chloride
- customThe organic phase was then dried
- customthe desiccant was removed by filtration
- customthe solvent was evaporated to dryness in vacuo
Sources & evidence
- ORD record
- ord-be156d9ed4784c38bd6c91c61d3abc48
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008488B2
Reaction notes
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