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Diisopropylamine → 2-(6-Cyano-1-hexyn-1-yl)adenosine

HRID 719085
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인쇄 미리보기

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HRID 719085 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(NC(C)C)(C)C.[C:28]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[CH:35])#[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][C:34]#[C:35][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 7912DiisopropylamineHCID 1696622-IodoadenosineHCID 117685266-Heptynenitrile

생성물 1

HCID 112109712-(6-Cyano-1-hexyn-1-yl)adenosine수율 55%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228
Dimethylformamide
용매

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온도
50 °C

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%).

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
  6. customto thereby yield a compound of the present invention as a pale yellow powder (yield: 217 mg, percent yield: 55%)

출처 및 근거

ORD 기록
ord-fe9b2120a8cd4a878c4844adcc2be5b0
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07132409B2

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