5-ethyl-N-{2-methyl-2-[4-(methyloxy)phenyl]propyl}-N-({4-[(trifluoromethyl)oxy]phenyl}methyl)-2-pyrimidinamine | 596115-21-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 5-ethyl-N-{2-methyl-2-[4-(methyloxy)phenyl]propyl}-N-({4-[(trifluoromethyl)oxy]phenyl}methyl)-2-pyrimidinamine
• 英文别名: 5-ethyl-N-[2-(4-methoxyphenyl)-2-methylpropyl]-N-[[4-(trifluoromethoxy)phenyl]methyl]pyrimidin-2-amine
• CAS: 596115-21-8
• 化学式: C₂₅H₂₈F₃N₃O₂
• 分子量: 459.511
• InChiKey: HSPQSQSEZVEHJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-ethyl-N-{2-methyl-2-[4-(methyloxy)phenyl]propyl}-N-({4-[(trifluoromethyl)oxy]phenyl}methyl)-2-pyrimidinamine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以3.37 g的产率得到4-{2-[(5-ethyl-2-pyrimidinyl)({4-[(trifluoromethyl)oxy]phenyl}methyl)amino]-1,1-dimethylethyl}phenol
  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：

  5-ethyl-N-[2-methyl-2-[4-(methyloxy)phenyl]propyl]-2-pyrimidinamine 、 4-三氟甲氧基溴苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.05h， 生成 5-ethyl-N-{2-methyl-2-[4-(methyloxy)phenyl]propyl}-N-({4-[(trifluoromethyl)oxy]phenyl}methyl)-2-pyrimidinamine
  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