4-Chloro-2,5,6-trimethyl-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine | 86520-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-Chloro-2,5,6-trimethyl-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 4-chloro-2,5,6-trimethyl-7-phenylpyrrolo[2,3-d]pyrimidine
• CAS: 86520-45-8
• 化学式: C₁₅H₁₄ClN₃
• 分子量: 271.749
• InChiKey: SUOGWDSEKHQQGS-UHFFFAOYSA-N

物化性质

• 沸点：
  298.8±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  氰化钾 、 4-Chloro-2,5,6-trimethyl-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine 在 sodium 4-methylbenzenesulfinate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以86%的产率得到2,5,6-trimethyl-7-phenyl-7H-pyrrolo<2,3-d>pyrimidine-4-carbonitrile
  参考文献：
  名称：

  Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate

  摘要：

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.

  DOI：

  10.3987/com-94-s(b)38
• 作为产物：
  描述：

  2,5,6-trimethyl-3,7-dihydro-7-phenyl-4H-pyrrolo<2,3-d>pyrimidin-4-one 在 三氯氧磷 作用下， 反应 2.0h， 以99%的产率得到4-Chloro-2,5,6-trimethyl-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate

  摘要：

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.

  DOI：

  10.3987/com-94-s(b)38

文献信息

• Catalytic Action of Azolium Salts. IX. Synthesis of 6-Aroyl-9H-purines and Their Analogues by Nucleophilic Aroylation Catalyzed by Imidazolium or Benzimidazolium Salt.
  作者：Akira MIYASHITA、Yumiko SUZUKI、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.46.390

  日期：——

  In the presence of 1, 3-dimethylimidazolium iodide (1), 6-chloro-9-phenyl-9H-purine (7) and 4-chloro-5, 6-dimethylpyrrolo[2, 3-d]pyrimidines 40-42 undrwent uncleophilic aroylation with arenecarbaldehydes (5) to give the corresponding fused aroylpyrimidines 8 and 43-45. 1, 3-Dimethylbenzimidazolium iodide (2) was an effective catalyst for the similar synthesis of 7-aroyl-3-phenyl-3H-1, 2, 3-triazolo[4, 5-d]pyrimidines 16-21. In the synthesis of 4-aroyl-1H-pyrazolo[3, 4-d]pyrimidines 26-32, both azolium salts 1 and 2 were effective as catalysts. Moreover, 4-aroyl-7H-pyrrolo[2, 3-d]pyrimidines 43-45 were obtained in good yields via the 4-tosyl derivatives, in the presence of catalytic amounts of sodium p-toluenesulfinate (46) and the imidazolium salt 1. This catalytic aroylation was found to be a facile and useful method for the synthesis of 6-aroyl-9H-purines and their analogues.

  在1, 3-二甲基咪唑鎓碘化物（1）的存在下，6-氯-9-苯基-9H-嘌呤（7）和4-氯-5, 6-二甲基吡咯并[2, 3-d]嘧啶（40-42）与芳烃醛（5）发生亲核芳酰化反应，生成相应的融合芳酰嘧啶（8和43-45）。1, 3-二甲基苯并咪唑鎓碘化物（2）是合成7-酰基-3-苯基-3H-1, 2, 3-三唑并[4, 5-d]嘧啶（16-21）的有效催化剂。在合成4-酰基-1H-吡唑并[3, 4-d]嘧啶（26-32）中，咪唑盐（1和2）均表现出良好的催化效果。此外，通过4-托磺酸衍生物，在催化量的对甲苯磺酸钠（46）和咪唑盐（1）的存在下，获得了良好产率的4-酰基-7H-吡咯并[2, 3-d]嘧啶（43-45）。这种催化芳酰化反应被发现是一种简便而有效的方法，用于合成6-酰基-9H-嘌呤及其类似物。
• Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate
  作者：Akira Miyashita、Yumiko Suzuki、Kiyono Ohta、Takeo Higashino

  DOI：10.3987/com-94-s(b)38

  日期：——

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.