Reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])=[O:9])=[CH:6][N:5]=[C:4](SC)[N:3]=1.Cl[C:21]1C=CC=C(C(OO)=O)C=1.[S:31]([O-:34])(O)=[O:32].[Na+]>C(Cl)(Cl)Cl>[CH3:21][S:31]([C:4]1[N:3]=[C:2]([CH3:1])[C:7]([C:8]([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])=[O:9])=[CH:6][N:5]=1)(=[O:34])=[O:32]Participants
Procedure
To 20 ml of chloroform was dissolved 1.10 g (3.8 mmol) of 4,4-difluoro-3-methyl-3-butenyl 4-methyl-2-(methylthio)pyrimidine-5-carboxylate, followed by the addition, in three portions, of 2.00 g (8.1 mmol) of 70% m-chloroperbenzoic acid under ice-cooling and stirring for 1 hour after warming to room temperature. An aqueous solution of sodium hydrogensulfite was added under ice-cooling and the mixture was filtered to fractionate an organic layer. The organic layer was washed with a saturated sodium hydrogencarbonate solution and water in this order, followed by drying over anhydrous magnesium sulfate, the addition of “Florisil” and filtering. The solution was concentrated at 40° C. under reduced pressure to obtain 1.13 g (yield: 92%) of 4,4-difluoro-3-methyl-3-butenyl 2-methanesulfonyl-4-methylpyrimidine-5-carboxylate.
Workup
- temperaturecooling
- temperaturecooling
- filtrationthe mixture was filtered
- washThe organic layer was washed with a saturated sodium hydrogencarbonate solution and water in this order
- dry with materialby drying over anhydrous magnesium sulfate
- additionthe addition of “Florisil”
- filtrationfiltering
- concentrationThe solution was concentrated at 40° C. under reduced pressure
Sources & evidence
- ORD record
- ord-ffa3667fcdf5442a91df2ab16e44f8f3
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07273878B2
Linked notes
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