Potassium Carbonate → 7-(4-Fluorophenyl)-2-(methylsulfonyl)thieno[3,2-d]pyrimidine-6-carboxamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[S:10][C:9]=2[C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1.B1([O-])OO1.[OH2:26].[OH2:27].O.O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[N:13]=[C:14]([S:17]([CH3:18])(=[O:27])=[O:26])[N:15]=[CH:16][C:11]=3[S:10][C:9]=2[C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 135 mg of 7-(4-fluorophenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxamide and 293 mg of sodium perborate tetrahydrate in 5 ml of acetic acid is microwave-heated at 70° C. in a sealed tube for 1 h 30. The mixture is taken up with dichloromethane and 100 ml of a sodium thiosulfate solution. The pH is adjusted to pH 8-9 by adding solid potassium carbonate and the aqueous phase is extracted with dichloromethane. The organic phases are dried over magnesium sulfate, filtered, and then concentrated under vacuum so as to obtain a beige solid. This crude is purified on 40 g of silica, elution being carried out with dichloromethane, so as to obtain 90 mg of 7-(4-fluorophenyl)-2-(methylsulfonyl)thieno[3,2-d]pyrimidine-6-carboxamide in the form of a white solid.
Workup
- extractionthe aqueous phase is extracted with dichloromethane
- dry with materialThe organic phases are dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum so as
- customto obtain a beige solid
- customThis crude is purified on 40 g of silica, elution
Sources & evidence
- ORD record
- ord-d90349b41c374309adeac0fc0b733c66
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Reaction notes
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