4-chloro-2-phenylpyrimido[4,5-d]pyrimidine | 1256556-21-4

• 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: 4-chloro-2-phenylpyrimido[4,5-d]pyrimidine
• 英文别名: 4-Chloro-2-phenylpyrimido[4,5-d]pyrimidine
• CAS: 1256556-21-4
• 化学式: C₁₂H₇ClN₄
• 分子量: 242.667
• InChiKey: WWEZZAJDUJBVCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(5-cyanopyrimidin-4-yl)benzamide 在 五氯化磷 作用下， 以 环丁砜 为溶剂， 反应 3.0h， 以64%的产率得到4-chloro-2-phenylpyrimido[4,5-d]pyrimidine
  参考文献：
  名称：

  Convenient and Practical One-Pot Synthesis of 4-Chloropyrimidines via a Novel Chloroimidate Annulation

  摘要：

  Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.

  DOI：

  10.1021/op1002352

文献信息

• Convenient and Practical One-Pot Synthesis of 4-Chloropyrimidines via a Novel Chloroimidate Annulation
  作者：Thomas Storz、Richard Heid、Joseph Zeldis、Steven M. Hoagland、Vito Rapisardi、Susan Hollywood、George Morton

  DOI：10.1021/op1002352

  日期：2011.7.15

  Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.