Reaktion #84411

Reaktionsgleichung

methyl 3-acetaminocrotonate

3-fluoro-4-(1H-pyrazol-1-yl)aniline

trimethylaluminum

→

title compound

Ausbeute 38.2%

3-(3-fluoro-4-(1H-pyrazol-1-yl)phenyl)-2,6-dimethylpyrimidin-4(3H)-one

Ausbeute 38.2%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred at rt for 3 days
2. 2
   Sonstigequenched with saturated NH4Cl aqueous solution
3. 3
   Extraktionextracted with CH2Cl2 (100 mL×3)
4. 4
   TrocknenThe combined organic phases were dried over anhydrous Na2SO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:2)

Vorschrift

To a solution of 3-fluoro-4-(1H-pyrazol-1-yl)aniline (0.65 g, 3.68 mmol) in CH2Cl2 (30 mL) was added trimethylaluminum (18.4 mL, 36.8 mmol, 2 M in heptane) slowly. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (634 mg, 4.04 mmol) in CH2Cl2 (10 mL). The reaction was stirred at rt for 3 days, 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 (PE/EtOAc (V/V)=1:2) to give the title compound as a white solid (400 mg, 38%). The compound was characterized by the following spectroscopic data:

Quelle