反応 #84454

反応方程式

methyl 3-acetaminocrotonate

2-fluoro-N1,N1-bis(2-propoxyethyl)benzene-1,4-diamine

trimethylaluminum

→

title compound

収率 78.0%

3-(4-(bis(2-propoxyethyl)amino)-3-fluorophenyl)-2,6-dimethyl pyrimidin-4(3H)-one

収率 78.0%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 72 h
2. 2
   その他quenched with saturated NH4Cl aqueous solution
3. 3
   抽出extracted with CH2Cl2 (50 mL×3)
4. 4
   乾燥The combined organic phases were dried over anhydrous Na2SO4
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

実験手順

To a solution of 2-fluoro-N1,N1-bis(2-propoxyethyl)benzene-1,4-diamine (0.50 g, 1.68 mmol) in CH2Cl2 (10 mL) was added trimethylaluminum (3.4 mL, 6.8 mmol, 2 M in toluene) slowly. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (0.32 g, 2.02 mmol) in CH2Cl2 (2 mL). The reaction mixture was stirred at rt for 72 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 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)=2:1) to give the title compound as pale yellow oil (0.53 g, 78%). The compound was characterized by the following spectroscopic data:

出典