5-(1-hydroxy-2,2-dimethylpropyl)pyrimidine-2,4(1H,3H)-dione

• 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: 5-(1-hydroxy-2,2-dimethylpropyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-(1-hydroxy-2,2-dimethylpropyl)-1H-pyrimidine-2,4-dione
• 化学式: C₉H₁₄N₂O₃
• 分子量: 198.222
• InChiKey: GRJQKMYSEPIADV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-碘尿嘧啶 、 特戊醛 在 甲基氯化镁 、 lithium chloride 、 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以77%的产率得到5-(1-hydroxy-2,2-dimethylpropyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Functionalization of Unprotected Uracil Derivatives Using the Halogen−Magnesium Exchange

  摘要：

  The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl center dot LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5-functionalized uracil derivatives. This method was also successfully applied to the functionalization of 6-iodouracils including the synthesis of pharmaceutically relevant Emivirine and HEPT precursors.

  DOI：

  10.1021/ol063136w

文献信息

• Functionalization of Unprotected Uracil Derivatives Using the Halogen−Magnesium Exchange
  作者：Felix Kopp、Paul Knochel

  DOI：10.1021/ol063136w

  日期：2007.4.1

  The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl center dot LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5-functionalized uracil derivatives. This method was also successfully applied to the functionalization of 6-iodouracils including the synthesis of pharmaceutically relevant Emivirine and HEPT precursors.