2,4-diamino-6-(3-hydroxyprop-1-yn-1-yl)pyrimidine | 727651-48-1

• 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: 2,4-diamino-6-(3-hydroxyprop-1-yn-1-yl)pyrimidine
• 英文别名: 3-(2,6-Diaminopyrimidin-4-yl)prop-2-yn-1-ol
• CAS: 727651-48-1
• 化学式: C₇H₈N₄O
• 分子量: 164.167
• InChiKey: QQOOLDZKUDMDHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  98
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-diamino-6-(3-hydroxyprop-1-yn-1-yl)pyrimidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以78%的产率得到2,4-diamino-6-(3-hydroxypropyl)pyrimidine
  参考文献：
  名称：

  Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines

  摘要：

  准备了几种作为抗病毒活性的2,4-二氨基-6-[2-(磷酸甲氧基)乙氧基]嘧啶的饱和和不饱和的碳酰类似物6-[(磷酸甲氧基)烷基]嘧啶和6-[(磷酸甲氧基)炔基]嘧啶。它们的合成关键步骤是成功应用Sonogashira交叉偶联反应。将C-O基团替换为C-C键导致了生物活性的丧失。

  DOI：

  10.1135/cccc20050247
• 作为产物：
  描述：

  2,4-二氨基-6-碘嘧啶 、 2-丙炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以61%的产率得到2,4-diamino-6-(3-hydroxyprop-1-yn-1-yl)pyrimidine
  参考文献：
  名称：

  An efficient synthesis of cytostatic mono and bis-alkynylpyrimidine derivatives by the Sonogashira cross-coupling reactions of 2,4-diamino-6-iodopyrimidine and 2-amino-4,6-dichloropyrimidine

  摘要：

  A series of 6-alkynyl-2,4-diaminopyrimidine derivatives bearing various substituents at alkynyl moiety was prepared by the Sonogashira cross-coupling reaction of 2,4-diamino-6-iodopyrimidine using Pd(PPh3)(2)Cl-2 as catalyst. The same reaction was applied to 2-amino-4,6-dichloropyrimidine. This compound on reaction with 1 equiv. of alkyne gave 6-alkynyl-2-amino-4-chloropyrimidine derivatives as main products, while reaction with three equivalents of alkyne afforded predominantly 4,6-bis-alkynyl-2-aminopyrimidines. Some of the resulting alkynyl pyrimidines showed considerable cytostatic activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.035

文献信息

• Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines
  作者：Dana Hocková、Milena Masojídková、Antonín Holý

  DOI：10.1135/cccc20050247

  日期：——

  Several 6-[(phosphonomethoxy)alkyl]pyrimidines and 6-[(phosphonomethoxy)alkynyl]pyrimidines were prepared as saturated and unsaturated carba-analogues of antivirally active 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidine. As the key step of their synthesis the Sonogashira cross-coupling reaction was successfully applied. The replacement of the C-O moiety by the C-C bond resulted in the loss of biological activity.

  准备了几种作为抗病毒活性的2,4-二氨基-6-[2-(磷酸甲氧基)乙氧基]嘧啶的饱和和不饱和的碳酰类似物6-[(磷酸甲氧基)烷基]嘧啶和6-[(磷酸甲氧基)炔基]嘧啶。它们的合成关键步骤是成功应用Sonogashira交叉偶联反应。将C-O基团替换为C-C键导致了生物活性的丧失。
• An efficient synthesis of cytostatic mono and bis-alkynylpyrimidine derivatives by the Sonogashira cross-coupling reactions of 2,4-diamino-6-iodopyrimidine and 2-amino-4,6-dichloropyrimidine
  作者：Dana Hocková、Antonı́n Holý、Milena Masojı́dková、Ivan Votruba

  DOI：10.1016/j.tet.2004.04.035

  日期：2004.5

  A series of 6-alkynyl-2,4-diaminopyrimidine derivatives bearing various substituents at alkynyl moiety was prepared by the Sonogashira cross-coupling reaction of 2,4-diamino-6-iodopyrimidine using Pd(PPh3)(2)Cl-2 as catalyst. The same reaction was applied to 2-amino-4,6-dichloropyrimidine. This compound on reaction with 1 equiv. of alkyne gave 6-alkynyl-2-amino-4-chloropyrimidine derivatives as main products, while reaction with three equivalents of alkyne afforded predominantly 4,6-bis-alkynyl-2-aminopyrimidines. Some of the resulting alkynyl pyrimidines showed considerable cytostatic activity. (C) 2004 Elsevier Ltd. All rights reserved.