dibenzyl(2-n-ethyl-9-methyl-9H-purin-6-yl)amin | 1235863-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: dibenzyl(2-n-ethyl-9-methyl-9H-purin-6-yl)amin
• 英文别名: N,N-dibenzyl-2-ethyl-9-methylpurin-6-amine
• CAS: 1235863-03-2
• 化学式: C₂₂H₂₃N₅
• 分子量: 357.458
• InChiKey: LPORESFBCOCFKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二苯甲基-2-氯-9-甲基-9H-嘌呤-6-胺 、 三乙基硼 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 17.0h， 以87%的产率得到dibenzyl(2-n-ethyl-9-methyl-9H-purin-6-yl)amin
  参考文献：
  名称：

  Direct B-Alkyl Suzuki−Miyaura Cross-Coupling of 2-Halopurines. Practical Synthesis of ST1535, a Potent Adenosine A_2A Receptor Antagonist

  摘要：

  The scope and limitations of using palladium-catalyzed cross-coupling reactions of diverse butyl metal species with two different 2-halopurines were evaluated. While tributylboranes reacted readily and regioselectively with both 2-chloro-6-dibenzylaminopurines and 2-iodo-6-chloropurines, all the other alkyl metal species were much less reactive and gave very poor yield and/or selectivity of the desired product. This protocol was applied to the synthesis of an important adenosine A(2A) receptor antagonist, ST1535.

  DOI：

  10.1021/jo101027h

文献信息

• Development of a practical and sustainable strategy for the synthesis of ST1535 by an iron-catalyzed Kumada cross-coupling reaction
  作者：Francesca Bartoccini、Giovanni Piersanti、Silvia Armaroli、Alberto Cerri、Walter Cabri

  DOI：10.1016/j.tetlet.2014.01.030

  日期：2014.2

  A simple, convenient, and environmentally friendly route to ST1535 employing an iron-catalyzed cross-coupling reaction and butylmagnesium chloride is described. (C) 2014 Elsevier Ltd. All rights reserved.
• Direct B-Alkyl Suzuki−Miyaura Cross-Coupling of 2-Halopurines. Practical Synthesis of ST1535, a Potent Adenosine A_2A Receptor Antagonist
  作者：Francesca Bartoccini、Walter Cabri、Diana Celona、Patrizia Minetti、Giovanni Piersanti、Giorgio Tarzia

  DOI：10.1021/jo101027h

  日期：2010.8.6

  The scope and limitations of using palladium-catalyzed cross-coupling reactions of diverse butyl metal species with two different 2-halopurines were evaluated. While tributylboranes reacted readily and regioselectively with both 2-chloro-6-dibenzylaminopurines and 2-iodo-6-chloropurines, all the other alkyl metal species were much less reactive and gave very poor yield and/or selectivity of the desired product. This protocol was applied to the synthesis of an important adenosine A(2A) receptor antagonist, ST1535.