3-(4-(3-methoxyphenoxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline | 1236291-88-5

• 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-(3-methoxyphenoxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline
• 英文别名: 3-[4-(3-methoxyphenoxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]aniline
• CAS: 1236291-88-5
• 化学式: C₁₉H₁₆N₄O₂
• 分子量: 332.362
• InChiKey: PVXBFWPQKQQJQX-UHFFFAOYSA-N

物化性质

• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  86
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-(3-methoxyphenoxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到3-[[6-(3-氨基苯基)-7H-吡咯并[2,3-d]嘧啶-4-基]氧基]苯酚
  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
• 作为产物：
  描述：

  3-甲氧基苯酚 、 5-((3-aminophenyl)ethynyl)-6-chloropyrimidin-4-amine 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以74%的产率得到3-(4-(3-methoxyphenoxy)-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