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

HRID 586121
ノート
印刷プレビュー

反応式

HRID 586121 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 7912DiisopropylamineHCID 1696622-IodoadenosineHCID 117685266-Heptynenitrile

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228
Dimethylformamide
溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-27c42ac69cfb48788d060b2c2ee4d475
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06936596B2

反応ノート

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