Reaction #40952

Reaction equation

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

Pyridine-3-boronic acid

Na2CO3

2-(dicyclohexylphosphino)biphenyl

→

title compound

Yield 20.3%

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

Yield 20.3%

Solvents

DME water

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed for 3 hours
2. 2
   OtherThe solvents were evaporated under vacuum
3. 3
   Filtrationthe residue was filtered over a SCX cartridge
4. 4
   Washwashing with MeOH
5. 5
   Washeluting with MeOH/NH3 95:5
6. 6
   OtherThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (from 98-2-0.2 to 95:5:05)

Procedure

3-Benzoyl-1-(3-chloro-propyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep 41,500 mg, 1.2 mmol) was dissolved in degassed DME-water solution (5-1, 35 mL). Pyridine-3-boronic acid (629 mg, 1.8 mmol), Na2CO3 (380 mg, 3.6 mmol), 2-(dicyclohexylphosphino)biphenyl (84 mg, 0.24 mmol) and Pd(PPh3)4 (250 mg, 0.24 mmol) were added and the mixture was refluxed for 3 hours. The solvents were evaporated under vacuum and the residue was filtered over a SCX cartridge washing with MeOH and eluting with MeOH/NH3 95:5. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (from 98-2-0.2 to 95:5:05) to give the title compound (90 mg, 20% yield).

Source