Benzimidazolylpyrimidinediamine | 1140934-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: Benzimidazolylpyrimidinediamine
• 英文别名: 5-(1H-benzimidazol-2-yl)pyrimidine-2,4-diamine
• CAS: 1140934-55-9
• 化学式: C₁₁H₁₀N₆
• 分子量: 226.241
• InChiKey: BHQKIZFAYACFNY-UHFFFAOYSA-N

物化性质

• 沸点：
  630.7±65.0 °C(predicted)
• 密度：
  1.494±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(benzo[d]imidazol-2-yl)-3-(dimethylamino) acrylonitrile 、 胍 以 乙醇 为溶剂， 反应 28.0h， 以93%的产率得到Benzimidazolylpyrimidinediamine
  参考文献：
  名称：

  Synthesis of novel biaryl 2-benzimidazoles and 2-benzothiazoles

  摘要：

  Herein, we describe the synthesis of the novel 4-(1H-benzo[d]imidazol-2-yl)isoxazol-5-amine (7) and 4-(1H-benzo[d]thiazol-2-yl)isoxazol-5-amine scaffolds (8). Initial attempts following literature procedures for the synthesis of similar compounds did not yield the desired product. Instead we obtained the ring-opened adduct 2-(1H-benzo[d]imidazol-2(3H)-ylidene)-2-cyanoacetamide (5). We were able to modify reaction conditions and successfully synthesize the desired product. We also describe a convenient one-pot microwave-assisted relay reaction for the synthesis of novel and reported 2-substituted benzimidazoles and benzothiazoles from inexpensive, commercially available reagents, 2-benzothiazole acetonitrile (2) and 2-benzimidazole acetonitrile (1). In all cases, good yields of products were obtained and reaction times were significantly reduced. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.085

文献信息

• Synthesis of novel biaryl 2-benzimidazoles and 2-benzothiazoles
  作者：Kanaka Pattabiraman、Rita El-Khouri、Kriti Modi、Lawrence R. McGee、David Chow

  DOI：10.1016/j.tetlet.2009.01.085

  日期：2009.4

  Herein, we describe the synthesis of the novel 4-(1H-benzo[d]imidazol-2-yl)isoxazol-5-amine (7) and 4-(1H-benzo[d]thiazol-2-yl)isoxazol-5-amine scaffolds (8). Initial attempts following literature procedures for the synthesis of similar compounds did not yield the desired product. Instead we obtained the ring-opened adduct 2-(1H-benzo[d]imidazol-2(3H)-ylidene)-2-cyanoacetamide (5). We were able to modify reaction conditions and successfully synthesize the desired product. We also describe a convenient one-pot microwave-assisted relay reaction for the synthesis of novel and reported 2-substituted benzimidazoles and benzothiazoles from inexpensive, commercially available reagents, 2-benzothiazole acetonitrile (2) and 2-benzimidazole acetonitrile (1). In all cases, good yields of products were obtained and reaction times were significantly reduced. (C) 2009 Elsevier Ltd. All rights reserved.