2,4-二氨基-6-碘嘧啶 | 727651-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2,4-二氨基-6-碘嘧啶
• 英文名称: 2,4-diamino-6-iodopyrimidine
• 英文别名: 6-iodo-pyrimidine-2,4-diyldiamine；6-Jod-pyrimidin-2,4-diyldiamin；2,4-Diamino-6-iodopyrimidine；6-iodopyrimidine-2,4-diamine
• CAS: 727651-44-7
• 化学式: C₄H₅IN₄
• 分子量: 236.015
• InChiKey: CILZPFRDUNNUDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二氨基-6-碘嘧啶 在 水 、 锌 作用下， 生成 2,4-二氨基嘧啶
  参考文献：
  名称：

  Buettner, Chemische Berichte, 1903, vol. 36, p. 2234

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氨基-6-氯嘧啶 在 氢碘酸 、 sodium iodide 作用下， 生成 2,4-二氨基-6-碘嘧啶
  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.
• DE823452
  申请人：——

  公开号：——

  公开（公告）日：——
• Buettner, Chemische Berichte, 1903, vol. 36, p. 2234
  作者：Buettner

  DOI：——

  日期：——
• Efficient Synthesis of Pyrimidinecarbonitriles and Their Derivatives
  作者：Petra Doláková、Milena Masojídková、Antonín Holy

  DOI：10.3987/com-07-11014

  日期：——

  New approach to pyrimidinecarbonitriles was developed. Pyrimidine-4- and 6-carbonitriles were prepared by palladium-catalyzed cross-coupling reaction of iodopyrimidines with Zn(CN)2 in very good yields. The cyano group was converted into the corresponding acyl groups by the treatment with Grignard reagents and transformed to amido and imido function as well.