반응 #68818

반응 방정식

Triethylamine

triphenylphosphine

5-bromo-2-methylsulfanyl-pyrimidine

phenylacetylene

→

2-Methylsulfanyl-5-phenylethynyl-pyrimidine

용매

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   추출extracted once with saturated NaHCO3 solution and three times with ethyl acetate
3. 3
   건조dried with sodium sulfate
4. 4
   여과filtered
5. 5
   기타evaporated to dryness
6. 6
   기타The crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 100:0->50:50)

실험 절차

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+).

출처