Reaction #40959

Reaction equation

2,4-Di-methoxy-pyrimidine-5-boronic acid

2-bromo-6-methylpyridine

Na2CO3

PPh3

→

title compound

Yield 47.7%

2,4-Dimethoxy-5-(6-methyl-pyridin-2-yl)-pyrimidine

Yield 47.7%

Solvents

n-PrOH

Conditions

Workup

1. 1
   Temperatureat reflux for 4 hours
2. 2
   OtherThe solvent was evaporated
3. 3
   Otherthe crude was partitioned between water and Et2O
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 (2-8)

Procedure

2,4-Di-methoxy-pyrimidine-5-boronic acid (500 mg, 2.72 mmol) was dissolved in degassed n-PrOH (40 mL) and then 2-bromo-6-methylpyridine (660 mg, 3.8 mmol), Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 0.22 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated and the crude was partitioned between water and Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8) to give 300 mg of the title compound (47% yield).

Source