1,3-dimethyl-5H-indolo[3,2-d]pyrimidine-2,4-dione | 55832-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 1,3-dimethyl-5H-indolo[3,2-d]pyrimidine-2,4-dione
• 英文别名: 1,3-dimethyl-1,5-dihydro-pyrimido[5,4-b]indole-2,4-dione；1,3-Dimethyl-indolo[3,2-d]pyrimidine-2,4-dione；1,3-dimethyl-5H-pyrimido[5,4-b]indole-2,4-dione
• CAS: 55832-85-4
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: FEFLGAVMXVRMEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-dimethyl-5-(N-methylamino)pyrimidine-2,4-dione 在 palladium on activated charcoal 盐酸 、 硫酸 、 potassium carbonate 作用下， 以 二苯醚 、 乙醇 、 丙酮 为溶剂， 反应 24.0h， 生成 1,3-dimethyl-5H-indolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Studies on Pyrimidines: Synthesis of Pyrimidine-Annelated Heterocycles from 5-Amino-6-cyclohex-2-enyl-1, 3-dimethyl-uracil

  摘要：

  Treatment of 5-amino-6-cyclohex-2-enyl-1,3-dimethyl-uracil with pyridinium hydrotribromide or hexamethylenetetrammonium hydrotribromide furnished the corresponding linear heterocyclic 6-bromo-1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-diones in 90% yield. Reaction of the same educt with molecular bromine in chloroform afforded the bicyclic 9-bromo-1,3-dimethylhexahydrobicyclo [3.3.1]indole[3,2-d]pyrimidine-2,4-diones in 85% yield. Upon treatment of the above substrate with cold concentrated sulfuric acid, a mixture of 1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-dione (28%) and 1,3-dimethylhexahydrobicyclo [3.3.1]indolo[3,2-d]pyrimidine-2,4-dione (60%) was obtained.

  DOI：

  10.1007/s007060170100

文献信息

• Neue Pyridazino-, Pyrimido-, Pyrazino- und Triazino-indole
  申请人：BAYER AG

  公开号：EP0802198A2

  公开（公告）日：1997-10-22

  Die erfindungsgemäßen Pyridazino-, Pyrimido-, Pyrazino- und Triazino-indole werden hergestellt durch Umsetzung der mit den entsprechenden Heterocyclen substituierten Phenylessigsäure-Derivaten gegebenenfalls in einer aktivierten Form mit Phenylglyzinolen. Die heterocyclisch kondensierten Indole eignen sich als Wirkstoffe in Arzneimittel, insbesondere in antiatherosklerotisch wirksamen Arzneimitteln.

  本发明中的哒嗪基、嘧啶基、吡嗪基和三嗪基吲哚是由相应杂环取代的苯乙酸衍生物（可选择活化形式）与苯基甘氨醇反应制备的。杂环缩合吲哚可作为药物的活性成分，特别是抗动脉粥样硬化药物。
• US5786361A
  申请人：——

  公开号：US5786361A

  公开（公告）日：1998-07-28
• Studies on Pyrimidines: Synthesis of Pyrimidine-Annelated Heterocycles from 5-Amino-6-cyclohex-2-enyl-1, 3-dimethyl-uracil
  作者：Krishna C. Majumdar、Nirmal K. Jana

  DOI：10.1007/s007060170100

  日期：2001.5.21

  Treatment of 5-amino-6-cyclohex-2-enyl-1,3-dimethyl-uracil with pyridinium hydrotribromide or hexamethylenetetrammonium hydrotribromide furnished the corresponding linear heterocyclic 6-bromo-1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-diones in 90% yield. Reaction of the same educt with molecular bromine in chloroform afforded the bicyclic 9-bromo-1,3-dimethylhexahydrobicyclo [3.3.1]indole[3,2-d]pyrimidine-2,4-diones in 85% yield. Upon treatment of the above substrate with cold concentrated sulfuric acid, a mixture of 1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-dione (28%) and 1,3-dimethylhexahydrobicyclo [3.3.1]indolo[3,2-d]pyrimidine-2,4-dione (60%) was obtained.