反应详情

温度

65 °C

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+).

1. temperatureThe reaction mixture was cooled
2. extractionextracted once with saturated NaHCO3 solution and three times with ethyl acetate
3. dry with materialdried with sodium sulfate
4. filtrationfiltered
5. customevaporated to dryness
6. customThe crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 100:0->50:50)