N-[3-(2-chloropyrimidin-4-yl)-phenyl]-carbamic acid 1,1-dimethylethyl ester | 883199-27-7

• 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: N-[3-(2-chloropyrimidin-4-yl)-phenyl]-carbamic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl N-[3-(2-chloropyrimidin-4-yl)phenyl]carbamate
• CAS: 883199-27-7
• 化学式: C₁₅H₁₆ClN₃O₂
• 分子量: 305.764
• InChiKey: UJLHGVRATFSNIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[3-(2-chloropyrimidin-4-yl)-phenyl]-carbamic acid 1,1-dimethylethyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-{[3-(2-chloropyrimidin-4-yl)-phenyl]-amino}-3-oxopropanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of analogs of the phenylamino-pyrimidine type protein kinase C inhibitor CGP 60474 utilizing a Negishi cross-coupling strategy

  摘要：

  Analogs of 3-{4-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-pyridin-2-yl-amino}-propanol (CGP 60474) were synthesized as useful models for the evaluation of structure-activity relationships of phenylamino-pyrimidine-type protein kinase C inhibitors. The approach involved Pd-assisted cross-coupling as the key step. Negishi-type coupling was performed both with free amino functionalities and Boc-protected amines present and showed that the protection-cross-coupling-deprotection sequence leads to significantly higher yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.067
• 作为产物：
  描述：

  2,4-二氯嘧啶 、 甲基锂 、 N-(叔丁氧基羰基)-3-溴苯胺 以75%的产率得到N-[3-(2-chloropyrimidin-4-yl)-phenyl]-carbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis of analogs of the phenylamino-pyrimidine type protein kinase C inhibitor CGP 60474 utilizing a Negishi cross-coupling strategy

  摘要：

  Analogs of 3-{4-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-pyridin-2-yl-amino}-propanol (CGP 60474) were synthesized as useful models for the evaluation of structure-activity relationships of phenylamino-pyrimidine-type protein kinase C inhibitors. The approach involved Pd-assisted cross-coupling as the key step. Negishi-type coupling was performed both with free amino functionalities and Boc-protected amines present and showed that the protection-cross-coupling-deprotection sequence leads to significantly higher yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.067