Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1>C1COCC1>[CH3:22][S:21][C:17]1[N:18]=[C:19]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[CH:20]=[CH:15][N:16]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In THF, a phenoxide was prepared from 3-(trifluoromethyl)phenol (4.54 g, 0.0187×1.5 mol) was mixed with NaH (1.12 g (ca. 60% in mineral oil), 0.0187×1.5 mol), and 4-chloro-2-(methylthio)pyrimidine (Compound No. VII-1) (3.0 g, 0.0187 mol) was added thereto and the mixture was refluxed for about 10 hours. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, then recrystallized from a methanol/water system to obtain the intermediate compound.
Workup
- additionVII-1) (3.0 g, 0.0187 mol) was added
- temperaturethe mixture was refluxed for about 10 hours
- customThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
- customto separate an organic phase
- washThe organic phase was washed with aqueous saturated sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customrecrystallized from a methanol/water system
- customto obtain the intermediate compound
Sources & evidence
- ORD record
- ord-3d58caaef3e54ab9bff64df1e59b26f5
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723412
Linked notes
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