1-(4-chlorophenyl)-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 1-(4-Chlorophenyl)-4-propan-2-yloxypyrazolo[3,4-d]pyrimidine；1-(4-chlorophenyl)-4-propan-2-yloxypyrazolo[3,4-d]pyrimidine
• 化学式: C₁₄H₁₃ClN₄O
• 分子量: 288.736
• InChiKey: NKFVEXFCWYUSID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,6-二氯-5-嘧啶甲醛 在 sodium tert-pentoxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 1-(4-chlorophenyl)-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine
  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

• Synthesis of 1,4-Disubstituted Pyrazolo[3,4-d]pyrimidines from 4,6-Dichloropyrimidine-5-carboxaldehyde: Insights into Selectivity and Reactivity
  作者：Christie Morrill、Young-Choon Moon、Suresh Babu、Neil Almstead

  DOI：10.1055/s-0033-1338862

  日期：——

  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.