Reacción #68818

Ecuación de reacción

Triethylamine

triphenylphosphine

5-bromo-2-methylsulfanyl-pyrimidine

phenylacetylene

→

2-Methylsulfanyl-5-phenylethynyl-pyrimidine

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled
2. 2
   Extracciónextracted once with saturated NaHCO3 solution and three times with ethyl acetate
3. 3
   Secadodried with sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated to dryness
6. 6
   OtroThe crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 100:0->50:50)

Procedimiento

Bis-(triphenylphosphine)-palladium(II)dichloride (120 mg, 0.16 mmol, 0.05 equiv.) were dissolved in 50 ml THF and 5-bromo-2-methylsulfanyl-pyrimidine (840 mg, 4.1 mmol) and phenylacetylene (410 μl, 4.1 mmol, 1 equiv.) were added at room temperature. Triethylamine (1.36 ml, 12.3 mmol, 3 equiv.), triphenylphosphine (28 mg, 0.12 mmol, 0.03 equiv.) and copper(I)iodide (19 mg, 0.08 mmol, 0.03 equiv.) were added and the mixture was stirred for 3 hours at 65° C. The reaction mixture was cooled and extracted once with saturated NaHCO3 solution and three times with ethyl acetate. The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 100:0->50:50). The desired 2-Methylsulfanyl-5-phenylethynyl-pyrimidine was obtained as a light yellow solid (400 mg, 44%), MS: m/e=227.3 (M+H+).

Fuente