Reaction #40961

Reaction equation

5-Iodo-2,4-dimethoxy-pyrimidine

2-methylphenyl boronic acid

Na2CO3

PPh3

→

title compound

Yield 46.3%

2,4-Dimethoxy-5-o-tolyl-pyrimidine

Yield 46.3%

Solvents

n-PrOH

Conditions

Workup

1. 1
   Temperatureat reflux for 3 hours
2. 2
   OtherThe solvent was evaporated
3. 3
   Otherthe crude was partitioned between water and DCM
4. 4
   DryingThe organic phase was dried (Na2SO4)
5. 5
   Otherevaporated
6. 6
   OtherThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-9)

Procedure

5-Iodo-2,4-dimethoxy-pyrimidine (1 g, 3.75 mmol) was dissolved in degassed n-PrOH (25 mL) and then 2-methylphenyl boronic acid (766 mg, 3.8 mmol), Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 5.67 mmol) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-9) to give 400 mg of the title compound (46% yield).

Source