5-amino-2-methoxycarbonylsulfanyl-4-methylsulfanylthieno[2,3-d]pyrimidin-6-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 5-amino-2-methoxycarbonylsulfanyl-4-methylsulfanylthieno[2,3-d]pyrimidin-6-carboxylic acid methyl ester
• 英文别名: Methyl 5-amino-2-(2-methoxy-2-oxoethyl)sulfanyl-4-methylsulfanylthieno[2,3-d]pyrimidine-6-carboxylate
• 化学式: C₁₂H₁₃N₃O₄S₃
• 分子量: 359.451
• InChiKey: LFVDXIFSENQFLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  183
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  丙二腈,[氨基(甲硫基)亚甲基]- 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 216.0h， 生成 5-amino-2-methoxycarbonylsulfanyl-4-methylsulfanylthieno[2,3-d]pyrimidin-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and reactions of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐carbonitrile

  摘要：

  AbstractThe synthesis of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carbonitrile 4 is described. Compound 4 was reacted with various alkylants. The reaction with chloroacetic acid derivatives results in the formation of thieno[2,3‐d]pyrimidines 8. When methyl iodide was used 2,4,6‐tris(methylsul‐fanyl)pyrimidine‐5‐carbonitrile 5 was obtained. The substitution of the methylsulfanyl groups in compound 5 by several N‐nuclophiles leads to amino substituted pyrimidines.

  DOI：

  10.1002/jhet.5570390502

文献信息

• Selective nucleophilic replacement of the benzylsulfanyl group in 2,4-disulfanyl-substituted thieno[2,3-<i>d</i>]pyrimidin-6-carboxylic acid derivatives by secondary amines
  作者：Detlef Briel、Simon Drescher、Bodo Dobner

  DOI：10.1002/jhet.5570420514

  日期：2005.7

  Thieno[2,3-d]pyrimidines with benzylsulfanyl and allylsulfanyl group in the presence of other alkylsul-fanyl substituents react selectively under mild conditions with secondary amines under replacement of the benzyl or allyl residue whereas the other substituents remain intact. This enables the synthesis of different basic substituted derivatives with potentially biologically activity.

  在存在其他烷基硫代-芳基取代基的情况下，具有苄基硫烷基和烯丙基硫烷基的噻吩并[2,3- d ]嘧啶在温和的条件下与仲胺选择性地反应，取代了苄基或烯丙基残基，而其他取代基则保持完整。这使得能够合成具有潜在生物学活性的不同的碱性取代的衍生物。
• Synthesis and reactions of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐carbonitrile
  作者：Detlef Briel、Tanja Franz、Bodo Dobner

  DOI：10.1002/jhet.5570390502

  日期：2002.9

  AbstractThe synthesis of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carbonitrile 4 is described. Compound 4 was reacted with various alkylants. The reaction with chloroacetic acid derivatives results in the formation of thieno[2,3‐d]pyrimidines 8. When methyl iodide was used 2,4,6‐tris(methylsul‐fanyl)pyrimidine‐5‐carbonitrile 5 was obtained. The substitution of the methylsulfanyl groups in compound 5 by several N‐nuclophiles leads to amino substituted pyrimidines.