Reacción #1528395

Ecuación de reacción

water

2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene

→

2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline

Rendimiento 79.6%

Disolventes

acetic acid

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrobelow 35° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Filtraciónthe reaction solution was filtered through celite
4. 4
   workup.ADDITIONdiluted with ethyl acetate
5. 5
   Lavadothe organic layer was washed with saturated aqueous sodium chloride solution
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated

Procedimiento

To a mixture of 8.6 g of iron powder, 27 ml of acetic acid and 2.7 ml of water was added dropwise a solution of 8.6 g of 2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene in 23 ml of acetic acid while keeping the temperature of the reaction solution at or below 35° C. After the addition was finished, the stirring was continued for 2 hours and then the reaction solution was filtered through celite and diluted with ethyl acetate. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution and the organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica-gel column chromatography to give 6.46 g of 2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline.

Fuente