2-iso-propylamino-4-(trimethylsilylethynyl)pyrimidine | 876521-30-1

• 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-iso-propylamino-4-(trimethylsilylethynyl)pyrimidine
• 英文别名: 2-Pyrimidinamine, N-(1-methylethyl)-4-[(trimethylsilyl)ethynyl]-；N-propan-2-yl-4-(2-trimethylsilylethynyl)pyrimidin-2-amine
• CAS: 876521-30-1
• 化学式: C₁₂H₁₉N₃Si
• 分子量: 233.388
• InChiKey: DBAMMJWVPGAVFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-iso-propylamino-4-(trimethylsilylethynyl)pyrimidine 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 potassium permanganate 、 copper(l) iodide 、 碳酸氢钠 、 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 2.5h， 生成 1-(4-氟苯基)-2-[2-(丙烷-2-基氨基)嘧啶-4-基]乙烷-1,2-二酮
  参考文献：
  名称：

  An Efficient Route to 4-Aryl-5-pyrimidinylimidazoles via Sequential Functionalization of 2,4-Dichloropyrimidine

  摘要：

  Starting from 2,4-dichloropyrimidine, a concise synthetic route to medicinally important 4-aryl-5-pyrimidinylimidazoles is described. Sequential substitution of the 4- and 2-chloro groups using a regioselective Sonogashira coupling, followed by nucleophilic substitution, led to pyrimidinylalkyne derivatives, which were then oxidized to their corresponding 1,2-diketones. These 1,2-diketones, on cyclocondensation with ammonium acetate and an aldehyde, furnished the desired pyrimidinyl imidazoles in good overall yields.

  DOI：

  10.1021/ol052663x
• 作为产物：
  描述：

  异丙胺 、 2-氯-4-((三甲基甲硅烷基)乙炔基)嘧啶 生成 2-iso-propylamino-4-(trimethylsilylethynyl)pyrimidine
  参考文献：
  名称：

  An Efficient Route to 4-Aryl-5-pyrimidinylimidazoles via Sequential Functionalization of 2,4-Dichloropyrimidine

  摘要：

  Starting from 2,4-dichloropyrimidine, a concise synthetic route to medicinally important 4-aryl-5-pyrimidinylimidazoles is described. Sequential substitution of the 4- and 2-chloro groups using a regioselective Sonogashira coupling, followed by nucleophilic substitution, led to pyrimidinylalkyne derivatives, which were then oxidized to their corresponding 1,2-diketones. These 1,2-diketones, on cyclocondensation with ammonium acetate and an aldehyde, furnished the desired pyrimidinyl imidazoles in good overall yields.

  DOI：

  10.1021/ol052663x

文献信息

• An Efficient Route to 4-Aryl-5-pyrimidinylimidazoles via Sequential Functionalization of 2,4-Dichloropyrimidine
  作者：Xiaohu Deng、Neelakandha S. Mani

  DOI：10.1021/ol052663x

  日期：2006.1.1

  Starting from 2,4-dichloropyrimidine, a concise synthetic route to medicinally important 4-aryl-5-pyrimidinylimidazoles is described. Sequential substitution of the 4- and 2-chloro groups using a regioselective Sonogashira coupling, followed by nucleophilic substitution, led to pyrimidinylalkyne derivatives, which were then oxidized to their corresponding 1,2-diketones. These 1,2-diketones, on cyclocondensation with ammonium acetate and an aldehyde, furnished the desired pyrimidinyl imidazoles in good overall yields.