Reaction #1810802

Reaction equation

2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenol

potassium carbonate

methyl 2-bromopropionate

→

methyl 2-[2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl) -1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]propionate

Yield 83.3%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   workup.STIRRINGthe mixture was stirred at 80° C. for 3 hours
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic layer was washed with saturated aqueous sodium chloride solution
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated

Procedure

Into 6 ml of N,N-dimethylformamide was dissolved 0.23 g of 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenol. After adding 0.22 g of anhydrous potassium carbonate, 0.13 g of methyl 2-bromopropionate was added at room temperature with stirring and then the mixture was stirred at 80° C. for 3 hours. After cooling the reaction solution to room temperature, the reaction solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica-gel column chromatography to give 0.23 g of methyl 2-[2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl) -1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]propionate [Compound A-3].

Source