2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(3-fluoro-4-((2-morpholinoethyl)amino)phenyl)-2,6-dimethyl pyrimidin-4(3H)-one
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C[Al](C)C.[NH:22](/[C:26](/[CH3:32])=[CH:27]\[C:28](OC)=[O:29])[C:23]([CH3:25])=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:28](=[O:29])[CH:27]=[C:26]([CH3:32])[N:22]=[C:23]2[CH3:25])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 2-fluoro-N1-(2-morpholinoethyl)benzene-1,4-diamine (0.50 g, 2.09 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (3.2 mL, 6.40 mmol, 2 M in toluene) slowly at rt. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (0.65 g, 4.13 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred at rt for 36 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (100 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=30:1) to give the title compound as a white solid (0.50 g, 24%). The compound was characterized by the following spectroscopic data:
Aufarbeitung
- stirringThe reaction mixture was stirred at rt for 36 h
- customquenched with saturated NH4Cl aqueous solution
- extractionextracted with CH2Cl2 (100 mL×3)
- dry with materialThe combined organic phases were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=30:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-738b2cbda2a04d41a39f2d384bb3c46c
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09434695B2
Notizen zur Reaktion
Wird geladen…