6-chloro-2-(3,5-dimethylpyrazol-1-yl)-N-pyrazin-2-ylpyrimidin-4-amine | 1522207-24-4

• 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: 6-chloro-2-(3,5-dimethylpyrazol-1-yl)-N-pyrazin-2-ylpyrimidin-4-amine
• CAS: 1522207-24-4
• 化学式: C₁₃H₁₂ClN₇
• 分子量: 301.738
• InChiKey: AWCHGHUMRKRDPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-(甲氧基甲基)吡咯烷盐酸盐 、 6-chloro-2-(3,5-dimethylpyrazol-1-yl)-N-pyrazin-2-ylpyrimidin-4-amine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 [2-(3,5-dimethylpyrazol-1-yl)-6-((R)-2-methoxymethylpyrrolidin-1-yl)pyrimidin-4-yl]pyrazin-2-ylamine
  参考文献：
  名称：

  Replacement of amide with bioisosteres led to a new series of potent adenosine A2A receptor antagonists

  摘要：

  We have previously reported a series of 2,4,6-trisubstituted pyrimidines as potent A(2A) receptor antagonists. The leading compounds often feature a potentially labile acetamide functional group which tends to hydrolyze under acidic conditions. Here we report the replacement of the acetamide functional group with bioisosteres. This effort led us to a new series of adenosine A(2A) receptor antagonists with improved potency and chemical stability. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.051
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 6-chloro-2-(methylsulfonyl)-N-(pyrazin-2-yl)pyrimidin-4-amine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 6-chloro-2-(3,5-dimethylpyrazol-1-yl)-N-pyrazin-2-ylpyrimidin-4-amine
  参考文献：
  名称：

  Replacement of amide with bioisosteres led to a new series of potent adenosine A2A receptor antagonists

  摘要：

  We have previously reported a series of 2,4,6-trisubstituted pyrimidines as potent A(2A) receptor antagonists. The leading compounds often feature a potentially labile acetamide functional group which tends to hydrolyze under acidic conditions. Here we report the replacement of the acetamide functional group with bioisosteres. This effort led us to a new series of adenosine A(2A) receptor antagonists with improved potency and chemical stability. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.051