Реакция #84405

Уравнение реакции

methyl 3-acetaminocrotonate

2-fluoro-5-morpholinoaniline

trimethylaluminum

→

title compound

Выход 69.0%

3-(2-fluoro-5-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-one

Выход 69.0%

Растворители

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt overnight
2. 2
   Другоеquenched with saturated NH4Cl aqueous solution (80 mL)
3. 3
   Экстракцияextracted with CH2Cl2 (100 mL×3)
4. 4
   ПромывкаThe combined organic phases were washed with brine (150 mL)
5. 5
   Сушкаdried over anhydrous Na2SO4
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   ДругоеThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:2)

Методика

To a solution of 2-fluoro-5-morpholinoaniline (0.35 g, 1.78 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (3.3 mL, 6.6 mmol, 2 M in toluene) dropwise. The reaction mixture was stirred at rt for 20 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (0.30 g, 1.78 mmol) in anhydrous CH2Cl2 (10 mL). The reaction mixture was stirred at rt overnight, then quenched with saturated NH4Cl aqueous solution (80 mL) and extracted with CH2Cl2 (100 mL×3). The combined organic phases were washed with brine (150 mL), 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 yellow solid (0.37 g, 69%). The compound was characterized by the following spectroscopic data:

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