2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzo[d]oxazole | 1429924-56-0

• 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: 2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzo[d]oxazole
• 英文别名: 2-(4-Chloropyrazolo[3,4-d]pyrimidin-1-yl)-1,3-benzoxazole
• CAS: 1429924-56-0
• 化学式: C₁₂H₆ClN₅O
• 分子量: 271.666
• InChiKey: DQWQMCURMFEYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-{2-[(4,6-dichloropyrimidin-5-yl)methylene]hydrazinyl}benzo[d]oxazole 以 乙腈 为溶剂， 反应 0.33h， 以92%的产率得到2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzo[d]oxazole
  参考文献：
  名称：

  Synthesis of 1,4-Disubstituted Pyrazolo[3,4-d]pyrimidines from 4,6-Dichloropyrimidine-5-carboxaldehyde: Insights into Selectivity and Reactivity

  摘要：

  Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5-carboxaldehyde with both aromatic and aliphatic hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective, high-yielding, and operationally simple manner are presented. For aromatic hydrazines, the reaction is performed at a high temperature in the absence of an external base. For aliphatic hydrazines, the reaction proceeds at room temperature in the presence of an external base. The observed selectivity and reactivity trends are rationalized through consideration of the proposed reaction mechanism. The 1-substituted 4-chloropyrazolo[3,4-d]pyrimidine products serve as versatile synthetic intermediates, through further functionalization of the 4-chloride moiety, enabling the rapid generation of a structurally diverse array of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines.

  DOI：

  10.1055/s-0033-1338862

文献信息

• Selective Synthesis of 1-Substituted 4-Chloropyrazolo[3,4-<i>d</i>]pyrimidines
  作者：Suresh Babu、Christie Morrill、Neil G. Almstead、Young-Choon Moon

  DOI：10.1021/ol4005382

  日期：2013.4.19

  Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5-carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.