Reaction #40955

Reaction equation

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

2-methyl-pyridine 4-boronic acid

Na2CO3

2-(dicyclohexylphosphino)biphenyl

→

title compound

Yield 25.1%

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

Yield 25.1%

Solvents

DME water

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed for 6 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 was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) and SCX cartridge
7. 7
   Washwashing with MeOH
8. 8
   Washeluting with MeOH/NH3 95:5

Procedure

3-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep 44, 433 mg, 1 mmol) was dissolved in degassed DME-water solution (5-1, 30 mL). 2-methyl-pyridine 4-boronic acid (205 mg, 1.5 mmol), Na2CO3 (212 mg, 2 mmol), 2-(dicyclohexylphosphino)biphenyl (70 mg, 0.2 mmol) and Pd(PPh3)4 (231 mg, 0.2 mmol) were added and the mixture was refluxed for 6 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 was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) and SCX cartridge washing with MeOH and eluting with MeOH/NH3 95:5 to give the title compound (100 mg, 25% yield).

Source