تفاعل #84405

معادلة التفاعل

methyl 3-acetaminocrotonate

2-fluoro-5-morpholinoaniline

trimethylaluminum

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title compound

المردود 69.0%

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

المردود 69.0%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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:

المصدر