Sodium Carbonate → 6-(2-fluoropyridin-4-yl)-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one
Reaktionsgleichung
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[NH:5][C:4]=2[CH:3]=1.[F:14][C:15]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:14][C:15]1[CH:20]=[C:19]([C:2]2[S:10][C:9]3[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[NH:5][C:4]=3[CH:3]=2)[CH:18]=[CH:17][N:16]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
A mixture of 6-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.052 g, 0.20 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.085 g, 0.60 mmol), 2 M sodium carbonate (0.30 mL, 0.60 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane adduct (0.033 g, 0.040 mmol) in 1,4-dioxane (2 mL) was degassed with nitrogen and heated at 70° C. for 15 h. Then, the reaction was cooled to room temperature, and concentrated with silica gel (2 mL), and the residue was purified by flash chromatography (silica gel, ethyl acetate to 80:20 ethyl acetate/methanol) to give the title compound (0.038 g, 69%) as a yellow solid:
Aufarbeitung
- customwas degassed with nitrogen
- temperatureThen, the reaction was cooled to room temperature
- concentrationconcentrated with silica gel (2 mL)
- customthe residue was purified by flash chromatography (silica gel, ethyl acetate to 80:20 ethyl acetate/methanol)
Quellen und Nachweise
- ORD-Eintrag
- ord-c4e725f8d6814af4a39884fc528f3038
- Quelldatensatz
- uspto-grants-2014_04
- Patentnummer
- US08691828B2
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