Reaktion #84536

Reaktionsgleichung

(Z)-methyl-3-(2-(3-fluorophenoxy)acetamido)but-2-enoate

3-fluoro-4-(4-methylpiperazin-1-yl)aniline

trimethylaluminium

→

title compound

Ausbeute 73.7%

3-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-2-((3-fluorophenoxy)methyl)-6-methylpyrimidin-4(3H)-one

Ausbeute 73.7%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting mixture was stirred at rt for 12 h
2. 2
   SonstigeThe mixture was then quenched with saturated NH4Cl aqueous solution
3. 3
   Extraktionextracted with CH2Cl2 (50 mL×2)
4. 4
   WaschenThe combined organic phases were washed with brine (100 mL)
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Vorschrift

To a solution of 3-fluoro-4-(4-methylpiperazin-1-yl)aniline (0.63 g, 3.01 mmol) in DCM (15 mL) was added trimethylaluminium (5.3 mL, 10.6 mmol, 2 M in toluene) and the mixture was stirred at rt for 0.5 h. A solution of (Z)-methyl-3-(2-(3-fluorophenoxy)acetamido)but-2-enoate (0.80 g, 2.99 mmol) in DCM (5 mL) was added slowly and the resulting mixture was stirred at rt for 12 h. The mixture was then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (0.94 g, 73%). The compound was characterized by the following spectroscopic data:

Quelle