Réaction #40938

Équation de réaction

2,4-Di-tert-butoxy-pyrimidine-5-boronic acid

2-bromo-3-methylthiophene

Na2CO3

PPh3

→

title compound

Rendement 32.0%

2,4-Di-tert-butoxy-5-(3-methyl-thiophen-2-yl)-pyrimidine

Rendement 32.0%

Solvants

n-PrOH

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 2.5 hours
2. 2
   AutreThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe crude was dissolved in water
4. 4
   Extractionextracted with Et2O
5. 5
   SéchageThe organic phase was dried (Na2SO4)
6. 6
   Autreevaporated
7. 7
   AutreThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99)

Mode opératoire

2,4-Di-tert-butoxy-pyrimidine-5-boronic acid (500 mg, 1.75 mmol) was dissolved in n-PrOH (5 mL) and then 2-bromo-3-methylthiophene (236 μl, 2.1 mmol), Na2CO3 (556 mg, 5.25 mmol), PPh3 (133 mg, 0.52 mmol) and Pd(OAc)2 (40 mg, 0.17 mmol) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated and the crude was dissolved in water and extracted with Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99) to give 170 mg of the title compound as a white solid (32% yield).

Source