Reaction #41027

Reaction equation

3-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione

2-Fluoro-pyridine 3-boronic acid

Na2CO3

2-(dicyclohexylphosphino)biphenyl

→

title compound

Yield 54.3%

3-Benzoyl-1-(4-chloro-butyl)-5-(2-fluoro-pyridin-3-yl)-1H-pyrimidine-2, 4-dione

Yield 54.3%

Solvents

DME water

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed for 3 hours
2. 2
   OtherThe solvents were evaporated under vacuum
3. 3
   Otherthe crude was partitioned between ethyl acetate and water
4. 4
   DryingThe organic phase was dried (Na2SO4)
5. 5
   Otherevaporated
6. 6
   Otherthe crude (0.9 g, yellow oil) was purified by flash chromatography with ethyl acetate-petroleum ether (1-1)

Procedure

3-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep129, 614 mg, 1.42 mmol) was dissolved in degassed DME-water solution (5-1, 35 ml). 2-Fluoro-pyridine 3-boronic acid (250 mg, 1.77 mmol), Na2CO3 (301 mg, 2.84 mmol), 2-(dicyclohexylphosphino)biphenyl (99 mg, 0.28 mmol) and Pd(PPh3)4 (328 mg, 0.28 mmol) were added and the mixture was refluxed for 3 hours. The solvents were evaporated under vacuum and the crude was partitioned between ethyl acetate and water. The organic phase was dried (Na2SO4) and evaporated; the crude (0.9 g, yellow oil) was purified by flash chromatography with ethyl acetate-petroleum ether (1-1) to give the title compound as yellow oil (310 mg, 54% yield).

Source