Acetonitrile → Methyl 7-[2-(difluoromethoxy)phenyl]-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate
Reaction equation
Cl[C:2]1[C:3]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH:19]([F:21])[F:20])=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[SH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])[O-].[K+].[K+].C(#N)C>Cl>[F:20][CH:19]([F:21])[O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[C:3]2[N:4]=[C:5]([S:8][CH3:9])[N:6]=[CH:7][C:2]=2[S:22][C:23]=1[C:24]([O:26][CH3:27])=[O:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 303 mg of [5-chloro-2-(methylsulfanyl)pyrimidin-4-yl][2-(difluoromethoxy)phenyl]methanone 7, 107 mg of methyl sulfanylacetate, 253 mg of potassium carbonate and 5 ml of acetonitrile is microwave-heated in a sealed tube at 60° C. for 4 h. The mixture is diluted with a 0.5 N aqueous hydrochloric acid solution and extracted twice with ethyl acetate and once with dichloromethane. The organic phases are dried over magnesium sulfate, filtered, and then concentrated under vacuum so as to obtain 343 mg of methyl 7-[2-(difluoromethoxy)phenyl]-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate 8 in the form of a pale yellow solid.
Workup
- extractionextracted twice with ethyl acetate and once with dichloromethane
- dry with materialThe organic phases are dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum so as
Sources & evidence
- ORD record
- ord-c30190c514524476920a6348e593db24
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Reaction notes
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