Reaction equation
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].Cl[C:7]1[CH:12]=[C:11](Cl)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1>C1COCC1.CN(C=O)C>[CH2:1]([O:3][C:7]1[CH:12]=[C:11]([O:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:25])[F:26])[CH:19]=2)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1)[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Ethanol (1.18 g, 0.0256×1.0 mol) and NaH (1.02 g, (ca.60% in mineral oil), 0.0256×1.0 mol) were dissolved in THF and 4,6-dichloro-2-methylthiopyrimidine (Compound No. VII-23)(5.0 g, 0.0256 mol) was added thereto. The resulting solution was stirred for about 30 minutes at room temperature. To this reaction solution, m-trifluoromethyl-phenol (6.23 g, 0.0256×1.5 mol), NaH (1.54 g, (ca.60% in mineral oil), 0.0256×1.5 mol), and KI (2.12 g, 0.0256×0.5 mol) dissolved in DMF were added. The resulting solution was refluxed for about 7 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, and thereafter purified on a silica gel column.
Workup
- additionVII-23)(5.0 g, 0.0256 mol) was added
- additionwere added
- temperatureThe resulting solution was refluxed for about 7 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
- custompurified on a silica gel column
Sources & evidence
- ORD record
- ord-0c41a886f892437a80e1ebfc69bc8999
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723412
Linked notes
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