Reaktionsgleichung
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([NH2:20])=[CH:17][CH:18]=2)[CH:13]=[N:12]1.Cl>C(O)C>[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][C:2]3[N:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][N:3]=3)=[CH:17][CH:18]=2)[CH:13]=[N:12]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 2-chloro-4-(methylthio)pyrimidine (1.0 g, 6.2 mmol) and 1-methyl-1H-indazol-5-amine (1.0 g, 6.8 mmol) in 10 mL of ethanol was added 1 mL of concentrated hydrochloric acid at room temperature. The reaction mixture was heated at 80° C. for 5 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was cooled to room temperature to form a solid. The resulting solid was collected by filtration and rinsed with cold ethanol to afford 1-methyl-N-(4-(methylthio)pyrimidin-2-yl)-1H-indazol-5-amine, intermediate 11 (0.7 g, 41%). The resulting solid was dissolved in 20 mL of dichloromethane and treated with m-chloroperbenzoic acid (mCPBA, 0.9 g, 5.2 mmol) at room temperature. After being stirred for 12 hours at room temperature, the reaction mixture was extracted with dichloromethane (×3) and washed with brine. The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was slurrified with heptane and then collected by filtration to afford the desired intermediate 12 as a white solid (0.6 g, 77%).
Aufarbeitung
- customa reaction with LC-MS or thin layer chromatography (TLC)
- temperatureThe reaction mixture was cooled to room temperature
- customto form a solid
- filtrationThe resulting solid was collected by filtration
- washrinsed with cold ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-63cc732551294189b17ebd8ffdea199f
- Quelldatensatz
- uspto-grants-2014_10
- Patentnummer
- US08871778B2
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