N'-(2-tert-butylpyrimidin-5-yl)-N,N-dimethylformamidine | 874921-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N'-(2-tert-butylpyrimidin-5-yl)-N,N-dimethylformamidine
• 英文别名: N'-(2-tert-butylpyrimidin-5-yl)-N,N-dimethylmethanimidamide
• CAS: 874921-32-1
• 化学式: C₁₁H₁₈N₄
• 分子量: 206.291
• InChiKey: OPUJWLNSKKEFLA-UHFFFAOYSA-N

物化性质

• 沸点：
  289.6±32.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(2-tert-butylpyrimidin-5-yl)-N,N-dimethylformamidine 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 以89.7%的产率得到四苯基锡
  参考文献：
  名称：

  The Synthesis of a Novel Inhibitor of B-Raf Kinase

  摘要：

  A scaleable synthetic route to [4,7']bis-isoquinolinyl-1-yl-(2-tert-butyl-pyrimidine-5-yl)amine (1), an inhibitor of B-Raf kinase is described. The key step in the synthesis is the Pd-catalyzed Negishi coupling of 4-bromo-1-chloroisoquinoline with trifluoromethanesulfonic acid isoquinoline-7-yl ester to yield 1-chloro-[4,7']bis-isoquinolinyl. This intermediate is transformed to the desired drug substance in one additional step, by reaction with 2-tert-butyl-5-aminopyrimidine in the presence of NaH. A special focus was put on the finally successful removal of traces of Zn and Pd in the drug substance, which came from the Negishi coupling.

  DOI：

  10.1021/op0501601
• 作为产物：
  描述：

  [(E)-3-dimethylamino-2-(dimethylaminomethyleneamino)allylidene]dimethylammonium hexafluorophosphate 、 2,2-二甲基丙亚胺盐酸 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以56%的产率得到N'-(2-tert-butylpyrimidin-5-yl)-N,N-dimethylformamidine
  参考文献：
  名称：

  The Synthesis of a Novel Inhibitor of B-Raf Kinase

  摘要：

  A scaleable synthetic route to [4,7']bis-isoquinolinyl-1-yl-(2-tert-butyl-pyrimidine-5-yl)amine (1), an inhibitor of B-Raf kinase is described. The key step in the synthesis is the Pd-catalyzed Negishi coupling of 4-bromo-1-chloroisoquinoline with trifluoromethanesulfonic acid isoquinoline-7-yl ester to yield 1-chloro-[4,7']bis-isoquinolinyl. This intermediate is transformed to the desired drug substance in one additional step, by reaction with 2-tert-butyl-5-aminopyrimidine in the presence of NaH. A special focus was put on the finally successful removal of traces of Zn and Pd in the drug substance, which came from the Negishi coupling.

  DOI：

  10.1021/op0501601

文献信息

• The Synthesis of a Novel Inhibitor of B-Raf Kinase
  作者：Donatienne Denni-Dischert、Wolfgang Marterer、Markus Bänziger、Naeem Yusuff、David Batt、Tim Ramsey、Peng Geng、Walter Michael、Run-Ming B. Wang、Francis Taplin,、Richard Versace、David Cesarz、Lawrence B. Perez

  DOI：10.1021/op0501601

  日期：2006.1.1

  A scaleable synthetic route to [4,7']bis-isoquinolinyl-1-yl-(2-tert-butyl-pyrimidine-5-yl)amine (1), an inhibitor of B-Raf kinase is described. The key step in the synthesis is the Pd-catalyzed Negishi coupling of 4-bromo-1-chloroisoquinoline with trifluoromethanesulfonic acid isoquinoline-7-yl ester to yield 1-chloro-[4,7']bis-isoquinolinyl. This intermediate is transformed to the desired drug substance in one additional step, by reaction with 2-tert-butyl-5-aminopyrimidine in the presence of NaH. A special focus was put on the finally successful removal of traces of Zn and Pd in the drug substance, which came from the Negishi coupling.