1-cyclopropyl-2-hydroxy-2-((morpholin-4-yl)carbonyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide | 1042275-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 1-cyclopropyl-2-hydroxy-2-((morpholin-4-yl)carbonyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
• CAS: 1042275-09-1
• 化学式: Br*C₁₄H₁₉N₄O₃
• 分子量: 371.234
• InChiKey: OOIBELIIGBJNHE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-2-hydroxy-2-((morpholin-4-yl)carbonyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以98%的产率得到N-cyclopropyl-4-(morpholin-4-ylcarbonyl)-1H-imidazol-2-ylamine
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758
• 作为产物：
  描述：

  N-环丙基-2-嘧啶胺 、 3-bromo-1-morpholin-4-ylpropane-1,2-dione 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以65%的产率得到1-cyclopropyl-2-hydroxy-2-((morpholin-4-yl)carbonyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758