Potassium Iodide → 2-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]pyrimidin-4-amine
Reaktionsgleichung
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[N:9][OH:10])[S:4][N:3]=1.Cl[CH2:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=1.[I-].[K+].N12CCCC1=NCCC2>C(#N)C>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](=[N:9][O:10][CH2:17][C:18]2[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=2)[C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[S:4][N:3]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred suspension of 1-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine (1.69 g, 6.06 mmol), 2-(chloromethyl)pyrimidin-4-amine (957 mg, 6.66 mmol) and potassium iodide (1.01 g, 6.06 mmol) in acetonitrile (15 mL) at 0° C. was added 1,5-diazabicyclo(4.3.0)non-5-ene (1.52 mL, 12.7 mmol). The mixture was stirred 10 min at 0° C., then overnight at room temperature. After dilution of the reaction mixture with water and extraction with ethyl acetate, the combined organic layers were dried over MgSO4, concentrated in vacuo, and the residue purified on silica gel to afford 2-[({[(3,4-dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]pyrimidin-4-amine [150 mg, yield 3%].
Aufarbeitung
- customovernight
- customat room temperature
- extractionAfter dilution of the reaction mixture with water and extraction with ethyl acetate
- dry with materialthe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
- customthe residue purified on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-7f50f8d852cb4ebe8d9afd7c0a114a51
- Quelldatensatz
- uspto-grants-2015_03
- Patentnummer
- US08981111B2
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