4,6-dimethyl-3-phenethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione | 914079-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 4,6-dimethyl-3-phenethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione
• 英文别名: 4,6-Dimethyl-3-(2-phenylethyl)triazolo[4,5-d]pyrimidine-5,7-dione；4,6-dimethyl-3-(2-phenylethyl)triazolo[4,5-d]pyrimidine-5,7-dione
• CAS: 914079-76-8
• 化学式: C₁₄H₁₅N₅O₂
• 分子量: 285.305
• InChiKey: FJAHMEWELCKKMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dimethyl-3-phenethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49%的产率得到8-Azacaffeine
  参考文献：
  名称：

  1H-或3H-[1,2,3]三唑并[4,5-d]嘧啶-5,7(4H,6H)-二酮(8-Azaxanthines)的合成和区域选择性N-和O-烷基化及其转化将它们的 3-烷基衍生物转化为 1-烷基异构体

  摘要：

  在非质子溶剂中使用了几种烷基化剂，例如卤代烷和硫酸二甲酯 在各种条件下用于单取代和双取代的 1H-或 3H-[1,2,3]三唑并[4,5-d]的烷基化嘧啶-5,7(4H,6H)-二酮，通过适当的 5,6-二氨基尿嘧啶与亚硝酸的环化制备。在无水碳酸钾存在下，三唑环上的烷基化同时在 1 位和 2 位发生，优先在 2 位烷基化。用等价的烷基化试剂在嘧啶环上进行类似的烷基化仅在 4 位发生。3,6-二取代衍生物在室温下烷基化导致5-O-烷基化伴随4-N-烷基化，但在高温下仅发生4-N-烷基化。3,4的反应，

  DOI：

  10.1055/s-2006-950337
• 作为产物：
  描述：

  6-methyl-3-phenethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到4,6-dimethyl-3-phenethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione
  参考文献：
  名称：

  Regioselective N- and O-Alkylation of 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (8-Azaxanthines) and Transformation of 3-Alkyl Derivatives into 1-Alkyl Isomers

  摘要：

  The alkylation on the pyrimidine ring of 3-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (1) with an equimolecular amount of alkylating agent in the presence of anhydrous potassium carbonate in aprotic solvents under heating took place only at the 4-position. The similar alkylation on the triazole ring of 6-methyl-1H-[1,2,3]triazolo[4,5-d]-pyrimidine5,7(4H,6H)-diones (4) with an equivalent alkylating reagent happened simultaneously at the 1- and 2-positions with the priority at the 2-position. On the other hand, the alkylation of 3,6-disubstituted derivatives (12a-d) at room temperature led to the 5-O-alkylation (14a-e) accompanied with the 4-N-alkylation (3a, 13a-d), but at high temperature only the 4-N-alkylation occurred. The 3,4,6-tri-substituted derivatives (3a, 13d) underwent transformation with excess alkylating agents at high temperature leading to the formation of 1,4,6-tri-substituted derivatives (7, 15) with elimination of the 3-substituent in the same manner as xanthine.

  DOI：

  10.3987/com-06-10807

文献信息

• Synthesis and Regioselective N- and O-Alkylation of 1<i>H</i>- or 3<i>H</i>-[1,2,3]Triazolo[4,5-<i>d</i>]pyrimidine-5,7(4<i>H</i>,6<i>H</i>)-diones (8-Azaxanthines) and Transformation of Their 3-Alkyl Derivatives into 1-Alkyl Isomers
  作者：Tomohisa Nagamatsu、Rafiqul Islam

  DOI：10.1055/s-2006-950337

  日期：——

  alkylating agents, for example alkyl halides and dimethyl sulfate, were employed in aprotic Solvents Under a variety of conditions for the alkylation of mono- and disubstituted 1H- or 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones, which were prepared by cyclization of the appropriate 5,6-diaminouracils with nitrous acid. The alkylation on the triazole ring in the presence of anhydrous potassium carbonate

  在非质子溶剂中使用了几种烷基化剂，例如卤代烷和硫酸二甲酯 在各种条件下用于单取代和双取代的 1H-或 3H-[1,2,3]三唑并[4,5-d]的烷基化嘧啶-5,7(4H,6H)-二酮，通过适当的 5,6-二氨基尿嘧啶与亚硝酸的环化制备。在无水碳酸钾存在下，三唑环上的烷基化同时在 1 位和 2 位发生，优先在 2 位烷基化。用等价的烷基化试剂在嘧啶环上进行类似的烷基化仅在 4 位发生。3,6-二取代衍生物在室温下烷基化导致5-O-烷基化伴随4-N-烷基化，但在高温下仅发生4-N-烷基化。3,4的反应，
• Regioselective N- and O-Alkylation of 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (8-Azaxanthines) and Transformation of 3-Alkyl Derivatives into 1-Alkyl Isomers
  作者：Tomohisa Nagamatsu、Rafiqul Islam

  DOI：10.3987/com-06-10807

  日期：——

  The alkylation on the pyrimidine ring of 3-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (1) with an equimolecular amount of alkylating agent in the presence of anhydrous potassium carbonate in aprotic solvents under heating took place only at the 4-position. The similar alkylation on the triazole ring of 6-methyl-1H-[1,2,3]triazolo[4,5-d]-pyrimidine5,7(4H,6H)-diones (4) with an equivalent alkylating reagent happened simultaneously at the 1- and 2-positions with the priority at the 2-position. On the other hand, the alkylation of 3,6-disubstituted derivatives (12a-d) at room temperature led to the 5-O-alkylation (14a-e) accompanied with the 4-N-alkylation (3a, 13a-d), but at high temperature only the 4-N-alkylation occurred. The 3,4,6-tri-substituted derivatives (3a, 13d) underwent transformation with excess alkylating agents at high temperature leading to the formation of 1,4,6-tri-substituted derivatives (7, 15) with elimination of the 3-substituent in the same manner as xanthine.