3-(4-(phenylthio)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline | 1236291-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(4-(phenylthio)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline
• 英文别名: 3-(4-phenylsulfanyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline
• CAS: 1236291-90-9
• 化学式: C₁₈H₁₄N₄S
• 分子量: 318.402
• InChiKey: CCGFUUXYOWMOIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-((3-aminophenyl)ethynyl)-6-chloropyrimidin-4-amine 、 苯硫酚 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以85%的产率得到3-(4-(phenylthio)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline
  参考文献：
  名称：

  Efficient formation of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines: a novel route to TWS119, a glycogen synthase kinase-3β inhibitor

  摘要：

  A concise synthesis of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines is described. The key step involves the formation of an ether or thioether linkage along with concurrent ring closure in one-pot to yield the desired product in only two steps from a common intermediate. The reaction is chemoselective to incorporate phenol, thiophenol, and thiol. This method enabled efficient production of TWS119, a glycogen synthase kinase-3 beta inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.032

文献信息

• Efficient formation of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines: a novel route to TWS119, a glycogen synthase kinase-3β inhibitor
  作者：Anand Mayasundari、Naoaki Fujii

  DOI：10.1016/j.tetlet.2010.05.032

  日期：2010.7

  A concise synthesis of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines is described. The key step involves the formation of an ether or thioether linkage along with concurrent ring closure in one-pot to yield the desired product in only two steps from a common intermediate. The reaction is chemoselective to incorporate phenol, thiophenol, and thiol. This method enabled efficient production of TWS119, a glycogen synthase kinase-3 beta inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.