Potassium tert-butoxide → 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-pyrimidine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[CH3:19][C:20]([CH3:23])([O-:22])[CH3:21].[K+]>C1COCC1.O>[Cl:8][C:6]1[CH:7]=[C:2]([O:22][C:20]([CH3:23])([CH3:21])[CH3:19])[N:3]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:5]=1Participants
5
Procedure
To a solution of 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step ii) (2 g) in THF (20 mL) was added potassium tert-butoxide (0.8 g) and the reaction mixture was stirred at ambient temperature for 20 h. Further potassium tert-butoxide (0.8 g) was added and the reaction mixture was stirred at ambient temperature for 4 h. The mixture was diluted with H2O and extracted with EtOAc (×3). The combined organic layers were washed with H2O and dried (MgSO4), filtered and evaporated. The resulting oil was purified by column chromatography on silica gel using MeOH/DCM (99:1 to 98:2 gradient) as eluent to give the subtitle compound as a clear, colourless oil. Yield: 0.68 g
Workup
- stirringthe reaction mixture was stirred at ambient temperature for 4 h
- extractionextracted with EtOAc (×3)
- washThe combined organic layers were washed with H2O
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe resulting oil was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-fc0fa91c77ed486094ff9dc2196f8e43
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722883B2
Reaction notes
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