2-ethoxy-3-ethyl-2(3H)-pyrimidinone

• 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: 2-ethoxy-3-ethyl-2(3H)-pyrimidinone
• 英文别名: 2-Ethoxy-3-ethylpyrimidin-4-one；2-ethoxy-3-ethylpyrimidin-4-one
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: NGLLNGFJSMMXPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫酸二乙酯 、 尿嘧啶 在 lithium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 以45%的产率得到1-乙基嘧啶-2,4(1H,3H)-二酮
  参考文献：
  名称：

  HSAB-driven chemoselective N1-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives

  摘要：

  The lithium salts of the conjugated bases of 4-methoxy- and 4-acetylamino-2(1H)-pyrimidinones 1-3 undergo highly chemoselective N-1-methylation or ethylation when treated with methyl- or ethylsulfate (hard electrophiles) in dry dioxane, while the use of DMF as solvent results in competitive O-2-alkylation. Potassium salts of the same bases in DMF undergo prevalent O-2-attack. Under the same conditions, a similar but less chemoselective behaviour is observed in alkylation of thymine and uracil, where some N-3 -attack occurs. This can be rationalised in terms of the HSAB principle. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.098

文献信息

• HSAB-driven chemoselective N1-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives
  作者：Augusto Gambacorta、Daniela Tofani、Maria Antonietta Loreto、Tecla Gasperi、Roberta Bernini

  DOI：10.1016/j.tet.2006.04.098

  日期：2006.7

  The lithium salts of the conjugated bases of 4-methoxy- and 4-acetylamino-2(1H)-pyrimidinones 1-3 undergo highly chemoselective N-1-methylation or ethylation when treated with methyl- or ethylsulfate (hard electrophiles) in dry dioxane, while the use of DMF as solvent results in competitive O-2-alkylation. Potassium salts of the same bases in DMF undergo prevalent O-2-attack. Under the same conditions, a similar but less chemoselective behaviour is observed in alkylation of thymine and uracil, where some N-3 -attack occurs. This can be rationalised in terms of the HSAB principle. (c) 2006 Elsevier Ltd. All rights reserved.