tetraethyl 2-aminopyrimidine-4,6-diyldiphosphonate | 1353054-72-4

• 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: tetraethyl 2-aminopyrimidine-4,6-diyldiphosphonate
• 英文别名: 4,6-Bis[diethoxy(oxido)phosphaniumyl]pyrimidin-2-amine；4,6-bis[diethoxy(oxido)phosphaniumyl]pyrimidin-2-amine
• CAS: 1353054-72-4
• 化学式: C₁₂H₂₃N₃O₆P₂
• 分子量: 367.279
• InChiKey: MVUPBXPBARPUDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氨基-4,6-二氯嘧啶 、 亚磷酸三乙酯 反应 0.33h， 以90%的产率得到tetraethyl 2-aminopyrimidine-4,6-diyldiphosphonate
  参考文献：
  名称：

  An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids

  摘要：

  Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.040

文献信息

• An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids
  作者：Petr Jansa、Ondřej Hradil、Ondřej Baszczyňski、Martin Dračínský、Blanka Klepetářová、Antonín Holý、Jan Balzarini、Zlatko Janeba

  DOI：10.1016/j.tet.2011.11.040

  日期：2012.1

  Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.