Réaction #40961

Équation de réaction

5-Iodo-2,4-dimethoxy-pyrimidine

2-methylphenyl boronic acid

Na2CO3

PPh3

→

title compound

Rendement 46.3%

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

Rendement 46.3%

Solvants

n-PrOH

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 3 hours
2. 2
   AutreThe solvent was evaporated
3. 3
   Autrethe crude was partitioned between water and DCM
4. 4
   SéchageThe organic phase was dried (Na2SO4)
5. 5
   Autreevaporated
6. 6
   AutreThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-9)

Mode opératoire

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