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Triethylamine → 2-(7-Cyano-1-heptynyl)-Adenosine

HRID 586124
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인쇄 미리보기

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HRID 586124 반응식
I[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].C(N(CC)CC)C.[C:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]#[CH:36])#[N:29]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]#[C:36][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])#[N:29]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 1696622-IodoadenosineHCID 131335007-Cyano-1-heptyne

생성물 1

HCID 695953062-(7-Cyano-1-heptynyl)-Adenosine수율 199.3%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

Under argon, to a solution of 2-iodoadenosine (200 mg, 0.51 mmol) and bis(triphenylphosphine)palladium dichloride (36 mg, 10 mol %) dissolved in N,N-dimethylformamide (5 mL), triethylamine (0.09 mL, 0.61 mmol, 1.2 eq.) and 7-cyano-1-heptyne (74 mg, 0.1 mmol, 1.2 eq.) were added, and, under ice-cooling conditions, cuprous iodide (10 mg, 5 mol %) was added thereto, followed by stirring at 60° 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 (chloroform:methanol=10:1), to thereby yield the above-titled compound as a pale yellow powder (yield: 77 mg, percent yield: 39%).

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified
  5. customby dry

출처 및 근거

ORD 기록
ord-3b80021d64b74106a8a6c624e16175f5
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06936596B2

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