Potassium Carbonate → 4-[8-(Difluoromethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile
Reaktionsgleichung
[OH:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:28]([F:33])([F:32])C([O-])=O.[Na+]>C(#N)C.C(Cl)(Cl)Cl>[F:32][CH:28]([F:33])[O:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
20 mg of the 4-(8-hydroxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile [158-1] was dissolved in 1 mL of acetonitrile, then 20 mg of potassium carbonate and 13 mg of sodium chlorodifluoroacetate were added, and stirred overnight at 90° C. After cooling the reaction mixture back to room temperature, diluted in 100 mL of chloroform, and washed with water and dried over anhydrous magnesium sulfate. The insolubles were filtered, then the filtrate was concentrated under reduced pressure and purified by preparative thin-layer chromatography, to obtain 15 mg of 4-[8-(difluoromethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [161-1] as a light brown solid.
Aufarbeitung
- temperatureAfter cooling the reaction mixture back to room temperature
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe insolubles were filtered
- concentrationthe filtrate was concentrated under reduced pressure
- custompurified by preparative thin-layer chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-f1a20971fa71487abda4ed54319cbc1c
- Quelldatensatz
- uspto-grants-2010_05
- Patentnummer
- US07718801B2
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