2-n-butyl-6-chloro-9-methyl-9H-purine | 1235863-00-9

• 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: 2-n-butyl-6-chloro-9-methyl-9H-purine
• 英文别名: 2-Butyl-6-chloro-9-methylpurine
• CAS: 1235863-00-9
• 化学式: C₁₀H₁₃ClN₄
• 分子量: 224.693
• InChiKey: NOQKLFARWRCRAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-n-butyl-6-chloro-9-methyl-9H-purine 在 氨 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以72%的产率得到2-butyl-9-methyladenine
  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
• 作为产物：
  描述：

  三丁基硼 、 6-chloro-2-iodo-9-methyl-9H-purine 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 、 水 为溶剂， 反应 7.0h， 以66%的产率得到2-n-butyl-6-chloro-9-methyl-9H-purine
  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

• CHEMICAL SYNTHESIS OF A HIGHLY POTENT EPOTHILONE
  申请人：Nicolaou Kyriacos C.

  公开号：US20110301183A1

  公开（公告）日：2011-12-08

  A highly active synthetic epothilone compound whose activity exceeds that of either epothilone EpoA or EpoB when assayed as a cytotoxic agent against a cancer cell line is disclosed as is a pharmaceutical composition containing the synthetic epothilone.
• 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.