Tert-butyl 4-[4-[bis(prop-2-enyl)amino]-5-fluoropyrimidin-2-yl]oxypiperidine-1-carboxylate | 1156437-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Tert-butyl 4-[4-[bis(prop-2-enyl)amino]-5-fluoropyrimidin-2-yl]oxypiperidine-1-carboxylate
• CAS: 1156437-51-2
• 化学式: C₂₀H₂₉FN₄O₃
• 分子量: 392.474
• InChiKey: DTEWJQXAZIUNDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-[4-[bis(prop-2-enyl)amino]-5-fluoropyrimidin-2-yl]oxypiperidine-1-carboxylate 在 lithium tert-butoxide 作用下， 以 二甲基亚砜 、 叔丁醇 为溶剂， 反应 1.0h， 生成 tert-butyl 4-((4-(di(prop-1-en-1-yl)amino)-5-fluoropyrimidin-2-yl)oxy)piperidine-1-carboxylate
  参考文献：
  名称：

  Practical Synthesis of 5-Fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine, a Key Intermediate in the Preparation of Potent Deoxycytidine Kinase Inhibitors

  摘要：

  A practical synthesis of 5-fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine, a key intermediate in the preparation of a new class of potent deoxycytidine kinase (dCK) inhibitors, is described. The commercially available 2,4-dichloro-5-fluoropyrimidine (12) is converted in four telescoped steps to tert-butyl 4-(4-amino-5- fluoropyrimidin-2-yloxy)piperidine-1-carboxylate (6a) which upon deprotection gives 5-fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine dihydrochloride (1a) in about 68% overall yield. This process proved to be an economical alternative to a Mitsunobu-based synthesis.

  DOI：

  10.1021/op900060u
• 作为产物：
  描述：

  2-chloro-5-fluoro-N,N-bis(prop-2-enyl)pyrimidin-4-amine 、 N-Boc-4-羟基哌啶 在 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 生成 Tert-butyl 4-[4-[bis(prop-2-enyl)amino]-5-fluoropyrimidin-2-yl]oxypiperidine-1-carboxylate
  参考文献：
  名称：

  Practical Synthesis of 5-Fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine, a Key Intermediate in the Preparation of Potent Deoxycytidine Kinase Inhibitors

  摘要：

  A practical synthesis of 5-fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine, a key intermediate in the preparation of a new class of potent deoxycytidine kinase (dCK) inhibitors, is described. The commercially available 2,4-dichloro-5-fluoropyrimidine (12) is converted in four telescoped steps to tert-butyl 4-(4-amino-5- fluoropyrimidin-2-yloxy)piperidine-1-carboxylate (6a) which upon deprotection gives 5-fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine dihydrochloride (1a) in about 68% overall yield. This process proved to be an economical alternative to a Mitsunobu-based synthesis.

  DOI：

  10.1021/op900060u