Реакция #84454

Уравнение реакции

methyl 3-acetaminocrotonate

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

trimethylaluminum

→

title compound

Выход 78.0%

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

Выход 78.0%

Растворители

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 72 h
2. 2
   Другоеquenched with saturated NH4Cl aqueous solution
3. 3
   Экстракцияextracted with CH2Cl2 (50 mL×3)
4. 4
   СушкаThe combined organic phases were dried over anhydrous Na2SO4
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Методика

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:

Источник