5-hydroxy-4-methoxy-7-(2-methoxyethyl)-5-methyl-2-(methylsulfanyl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 5-hydroxy-4-methoxy-7-(2-methoxyethyl)-5-methyl-2-(methylsulfanyl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
• 英文别名: 5-Hydroxy-4-methoxy-7-(2-methoxyethyl)-5-methyl-2-methylsulfanylpyrrolo[2,3-d]pyrimidin-6-one；5-hydroxy-4-methoxy-7-(2-methoxyethyl)-5-methyl-2-methylsulfanylpyrrolo[2,3-d]pyrimidin-6-one
• 化学式: C₁₂H₁₇N₃O₄S
• 分子量: 299.351
• InChiKey: JYOVBQYZSYTKKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-甲氧基-2-甲硫基-4-氯嘧啶 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 5-hydroxy-4-methoxy-7-(2-methoxyethyl)-5-methyl-2-(methylsulfanyl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
  参考文献：
  名称：

  Two-Step Synthesis of 5-Hydroxy-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one Derivatives from 4-Chloro-6-methoxy-2-(methylsulfanyl)pyrimidine

  摘要：

  We report a facile two-step procedure that allows the synthesis of the title fused heterocyclic derivatives from 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine, readily available from 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP). The first step is the lithiation at the 5-position of the starting material with lithium diisopropylamide (LDA) and the reaction of the resulting lithium compound with a-keto esters to give the corresponding 2-hydroxy-2-(pyrimidin-5-yl)carboxylic acid ester derivatives. In the second step, these are treated with primary aliphatic amines in the presence of triethylamine to afford the desired products.

  DOI：

  10.3987/com-15-13202

文献信息

• Two-Step Synthesis of 5-Hydroxy-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one Derivatives from 4-Chloro-6-methoxy-2-(methylsulfanyl)pyrimidine
  作者：Kazuhiro Kobayashi、Ryoga Ono、Shohei Yuba、Hidetaka Hiyoshi

  DOI：10.3987/com-15-13202

  日期：——

  We report a facile two-step procedure that allows the synthesis of the title fused heterocyclic derivatives from 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine, readily available from 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP). The first step is the lithiation at the 5-position of the starting material with lithium diisopropylamide (LDA) and the reaction of the resulting lithium compound with a-keto esters to give the corresponding 2-hydroxy-2-(pyrimidin-5-yl)carboxylic acid ester derivatives. In the second step, these are treated with primary aliphatic amines in the presence of triethylamine to afford the desired products.