Reaction #84405

Reaction equation

methyl 3-acetaminocrotonate

2-fluoro-5-morpholinoaniline

trimethylaluminum

→

title compound

Yield 69.0%

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

Yield 69.0%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

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

Procedure

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:

Source