2-[[4-[2-[(5-ethyl-2-pyrimidinyl)amino]-1,1-dimethylethyl]phenyl]oxy]-2-methylpropanoic acid | 1227056-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[[4-[2-[(5-ethyl-2-pyrimidinyl)amino]-1,1-dimethylethyl]phenyl]oxy]-2-methylpropanoic acid
• 英文别名: 2-[4-[1-[(5-Ethylpyrimidin-2-yl)amino]-2-methylpropan-2-yl]phenoxy]-2-methylpropanoic acid
• CAS: 1227056-72-5
• 化学式: C₂₀H₂₇N₃O₃
• 分子量: 357.453
• InChiKey: RDKUGYNUADSSCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  84.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[[4-[2-[(5-ethyl-2-pyrimidinyl)amino]-1,1-dimethylethyl]phenyl]oxy]-2-methylpropanoic acid 、 4-三氟甲氧基溴苄 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.17h， 以86%的产率得到2-[[4-[2-[(5-ethyl-2-pyrimidinyl)[[4-[(trifluoromethyl)oxy]phenyl]methyl]amino]-1,1-dimethylethyl]phenyl]oxy]-2-methylpropanoic acid
  参考文献：
  名称：

  Effects of Various Bases on Acid-Catalyzed Amination of 2-Chloro-5-ethylpyrimidine: Synthesis of PPARpan Agonist GW693085

  摘要：

  A unique buffering effect of various bases, i-Pr2NEt and CaCO3 in particular, was observed for the acid-catalyzed chloro displacement of 2-chloro-5-ethylpyrimidine with a 2-methyl-2-phenylpropanamine. The use of the carefully chosen bases was essential for the progression of the chloro displacement as well as the stability of the product in the presence of HCl formed. Research work leading to an efficient synthesis of PPARpan agonist GW693085 is described, featuring highly selective sequential N- and O-alkylations.

  DOI：

  10.1021/jo100562s
• 作为产物：
  描述：

  2-溴-2-甲基丙酸 、 4-[2-[(5-ethyl-2-pyrimidinyl)amino]-1,1-dimethylethyl]phenol 在 sodium hydroxide 作用下， 以 水 、 丁酮 为溶剂， 反应 3.0h， 以54.2 g的产率得到2-[[4-[2-[(5-ethyl-2-pyrimidinyl)amino]-1,1-dimethylethyl]phenyl]oxy]-2-methylpropanoic acid
  参考文献：
  名称：

  Effects of Various Bases on Acid-Catalyzed Amination of 2-Chloro-5-ethylpyrimidine: Synthesis of PPARpan Agonist GW693085

  摘要：

  A unique buffering effect of various bases, i-Pr2NEt and CaCO3 in particular, was observed for the acid-catalyzed chloro displacement of 2-chloro-5-ethylpyrimidine with a 2-methyl-2-phenylpropanamine. The use of the carefully chosen bases was essential for the progression of the chloro displacement as well as the stability of the product in the presence of HCl formed. Research work leading to an efficient synthesis of PPARpan agonist GW693085 is described, featuring highly selective sequential N- and O-alkylations.

  DOI：

  10.1021/jo100562s

文献信息

• Effects of Various Bases on Acid-Catalyzed Amination of 2-Chloro-5-ethylpyrimidine: Synthesis of PPARpan Agonist GW693085
  作者：Bobby N. Glover、Lynda A. Jones、Byron, S. Johnson、Alan Millar、Martin H. Osterhout、Shiping Xie

  DOI：10.1021/jo100562s

  日期：2010.6.4

  A unique buffering effect of various bases, i-Pr2NEt and CaCO3 in particular, was observed for the acid-catalyzed chloro displacement of 2-chloro-5-ethylpyrimidine with a 2-methyl-2-phenylpropanamine. The use of the carefully chosen bases was essential for the progression of the chloro displacement as well as the stability of the product in the presence of HCl formed. Research work leading to an efficient synthesis of PPARpan agonist GW693085 is described, featuring highly selective sequential N- and O-alkylations.