Reaktion #68818

Reaktionsgleichung

Triethylamine

triphenylphosphine

5-bromo-2-methylsulfanyl-pyrimidine

phenylacetylene

→

2-Methylsulfanyl-5-phenylethynyl-pyrimidine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled
2. 2
   Extraktionextracted once with saturated NaHCO3 solution and three times with ethyl acetate
3. 3
   Trocknendried with sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated to dryness
6. 6
   SonstigeThe crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 100:0->50:50)

Vorschrift

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+).

Quelle