Dimethyl Sulfoxide → (5-Chloro-2-(methylthio)pyrimidin-4-YL)(2-(difluoromethoxy)phenyl)methanone
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[C:13]([CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH:29]([F:31])[F:30])[OH:21])=[N:14][C:15]([S:18][CH3:19])=[N:16][CH:17]=1.C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[C:13]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH:29]([F:30])[F:31])=[O:21])=[N:14][C:15]([S:18][CH3:19])=[N:16][CH:17]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A solution of 78 mg of DMSO in 0.5 ml of dichloromethane is added slowly, under argon, to a solution of 75 mg of oxalyl chloride in 2 ml of dichloromethane, cooled to −78° C. After 20 min at −78° C., a solution of 308 mg of [5-chloro-2-(methylsulfanyl)pyrimidin-4-yl][2-(difluoromethoxy)phenyl]methanol 6 in 2 ml of dichloromethane is added. After 1 h 30 at −78° C., 182 mg of triethylamine are slowly added and the mixture is left to return to ambient temperature for 30 min. The mixture is then poured into water and extracted three times with dichloromethane. The organic phases are dried over magnesium sulfate, filtered, and then concentrated under vacuum so as to obtain 303 mg of [5-chloro-2-(methylsulfanyl)pyrimidin-4-yl][2-(difluoromethoxy)phenyl]methanone 7 in the form of a pale yellow oil.
Workup
- waitAfter 1 h 30 at −78° C.
- waitthe mixture is left
- waitto return to ambient temperature for 30 min
- extractionextracted three times with dichloromethane
- dry with materialThe organic phases are dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum so as
Sources & evidence
- ORD record
- ord-e6cc271a233748179f35533f35332089
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Reaction notes
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