2-ethoxy-4-methoxypyrimidine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethoxy-4-methoxypyrimidine
• 英文别名: 2-Ethoxy-4-methoxypyrimidine
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: YFZGAMINGYGCRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基-2(1H)-嘧啶酮 、 硫酸二乙酯 在 lithium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 以52%的产率得到1-ethyl-4-methoxy-2(1H)-pyrimidinone
  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

• Structure−Activity Relationship Studies on N³-Substituted Willardiine Derivatives Acting as AMPA or Kainate Receptor Antagonists
  作者：Nigel P. Dolman、Julia C. A. More、Andrew Alt、Jody L. Knauss、Helen M. Troop、David Bleakman、Graham L. Collingridge、David E. Jane

  DOI：10.1021/jm051086f

  日期：2006.4.1

  N3-substitution of the uracil ring of willardiine with a variety of carboxyalkyl or carboxybenzyl substituents produces AMPA and kainate receptor antagonists. In an attempt to improve the potency and selectivity of these AMPA and kainate receptor antagonists a series of analogues with different terminal acidic groups and interacidic group spacers was synthesized and pharmacologically characterized.

  威拉二因的尿嘧啶环被各种羧基烷基或羧基苄基取代基的 N3 取代产生 AMPA 和红藻氨酸受体拮抗剂。为了提高这些AMPA和红藻氨酸受体拮抗剂的效力和选择性，合成了一系列具有不同末端酸性基团和酸性基团间隔物的类似物并进行了药理学表征。(S)-1-(2-Amino-2-carboxyethyl)-3-(2-carboxythiophene-3-ylmethyl)pyrimidine-2,4-di one (43, UBP304) 对天然 GLU(K5 )-含红藻氨酸受体（K(D) 0.105 +/- 0.007 microM 与天然 GLU(K5) 上的红藻氨酸；K(D) 71.4 +/- 8.3 microM 与天然 AMPA 受体上的 (S)-5-氟威拉二碱）。在重组人 GLU(K5)、GLU(K5)/GLU(K6) 和 GLU(K5)/GLU(K2) 上，K(B) 值为 0.12 +/-
• 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.