반응 #806267

반응 방정식

diisopropylamine

6-cyano-1-hexyne

2-iodoadenosine

→

2-(6-cyano-1-hexyn-1-yl)adenosine

수율 55.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도The reaction mixture was cooled to room temperature
3. 3
   기타the solvent was removed under reduced pressure
4. 4
   기타The residue was purified
5. 5
   기타by dry
6. 6
   기타to thereby yield a compound of the present invention as a pale yellow powder (yield: 217 mg, percent yield: 55%)

실험 절차

Under argon, to a solution of 2-iodoadenosine (420 mg, 1.07 mmol) and bis(triphenylphosphine)palladium dichloride (75 mg, 10 mol %) dissolved in N,N-dimethylformamide (10 mL), diisopropylamine (0.18 mL, 1.28 mmol, 1.2 eq.) and 6-cyano-1-hexyne (137 mg, 1.28 mmol, 1.2 eq.) were added, and, under ice-cooling conditions, cuprous iodide (10 mg, 5 mol %) was added thereto, followed by stirring at 50° C. for 24 hours. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was purified by dry packed silica gel column chromatography (ethyl acetate:methanol=10:1), to thereby yield a compound of the present invention as a pale yellow powder (yield: 217 mg, percent yield: 55%).

출처