Hydrazine hydrate (1:1) → HCID 178490035, Verbindung
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10](=O)[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.COC(OC)[N:24]([CH3:26])C.O.[NH2:30]N>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=3)=[CH:26][NH:24][N:30]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1Komponenten
Versuchsvorschrift
1-(3-Methoxy-5-methylphenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone was heated with N,N-dimethylformamide dimethylacetal (34.46 mL, 258.6 mmol) at 90° C. for 20 hours with stirring. Excess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation, and the reaction mixture was dissolved in anhydrous ethanol (55 mL). To this solution was dropwise added hydrazine hydrate (2.59 mL, 51.72 mmol), and stirred at room temperature for 12 hours. After completion of the cyclization, the solvent was removed by vacuum distillation. The concentrate was treated in water and ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under vacuum. Purification by column chromatography gave the title compound (6.35 g, 78.6%).
Aufarbeitung
- customExcess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation
- dissolutionthe reaction mixture was dissolved in anhydrous ethanol (55 mL)
- stirringstirred at room temperature for 12 hours
- customAfter completion of the cyclization, the solvent was removed by vacuum distillation
- additionThe concentrate was treated in water
- dry with materialethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- distillationdistilled under vacuum
- customPurification by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-aa6270d22af2431185d5f409187206c5
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08273880B2
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