Reaction #44518

Reaction equation

6-(2-chloropyrimidin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide

3-methoxyaniline

→

title product

Yield 80.0%

6-(2-(3-methoxyphenylamino)pyrimidin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide

Yield 80.0%

Solvents

DMF

Conditions

Workup

1. 1
   Extractionsubjected to extraction with ethyl acetate
2. 2
   workup.ADDITIONThen water was added
3. 3
   Extractionthe mixture was subjected to extraction with ethyl acetate
4. 4
   WashThe organic layer was washed with water and brine sequentially
5. 5
   Dryingdried over anhydrous Na2SO4
6. 6
   Concentrationconcentrated
7. 7
   OtherThe resulting residue was purified by column chromatography

Procedure

6-(2-chloropyrimidin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide (0.1 mmol) and 3-methoxyaniline (0.1 mmol) were dissolved in 0.5 ml DMF. To this was added p-TsOH monohydrate (0.2 mmol). The reaction mixture was stirred at 60° C. for 5 hours, and subjected to extraction with ethyl acetate. Then water was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated. The resulting residue was purified by column chromatography to provide the title product in a yield of 80%.

Source