ethyl 5-bromo-6-methylpyrimidine-4-carboxylate | 1370725-12-4

• 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: ethyl 5-bromo-6-methylpyrimidine-4-carboxylate
• 英文别名: Ethyl 5-bromo-6-methylpyrimidine-4-carboxylate
• CAS: 1370725-12-4
• 化学式: C₈H₉BrN₂O₂
• 分子量: 245.076
• InChiKey: KXLCKKVPTNJXHS-UHFFFAOYSA-N

物化性质

• 沸点：
  316.5±37.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-bromo-6-methylpyrimidine-4-carboxylate 在 N-碘代丁二酰亚胺 、 palladium diacetate 、 caesium carbonate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-[(2S)-2,3-dihydroxypropyl]-5-(2-fluoro-4-iodoanilino)-6-methylpyrimidine-4-carboxamide
  参考文献：
  名称：

  Structure-based design and synthesis of bicyclic fused-pyridines as MEK inhibitors

  摘要：

  The MAPK pathway is identified as one of the most important pathways involved in cell proliferation and differentiation. A key kinase in the pathway, the Mitogen-activated protein kinase kinase (MEK) is recognized as a promising target for antitumor drugs. Structure-based design and optimization of known MEK inhibitors resulted in identification of compound 10a as a potent non-ATP competitive MEK inhibitor in both in vitro and in vivo tests. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.086
• 作为产物：
  描述：

  乙基6-甲基-4-嘧啶羧酸酯 在 溴 作用下， 以 乙醇 为溶剂， 生成 ethyl 5-bromo-6-methylpyrimidine-4-carboxylate
  参考文献：
  名称：

  [EN] REV-ERB AGONISTS FOR TH17-MEDIATED INFLAMMATORY DISORDERS
  [FR] AGONISTES REV-ERB POUR DES TROUBLES INFLAMMATOIRES À MÉDIATION PAR TH17

  摘要：

  The present disclosure provides compounds and their pharmaceutical compositions as selective agonists of REV-ERBα. The compounds are useful in various methods and uses, such as in the treatment of diseases including hyperglycemia, dyslipidemia, atherosclerosis, and autoimmune and inflammatory disorders or diseases, and as cancer therapeutics, such as for the treatment of glioblastoma, hepatocellular carcinoma, and colorectal cancer, and for immune-oncology purposes.

  公开号：

  WO2023122093A1

文献信息

• A Facile Synthesis of 5-Halopyrimidine-4-Carboxylic Acid Esters via a Minisci Reaction
  作者：Collin Regan、Fabrice Pierre、Michael Schwaebe、Mustapha Haddach、Michael Jung、David Ryckman

  DOI：10.1055/s-0031-1290136

  日期：2012.2

  This paper reports the synthesis of various 5-halopyrimidine-4-carboxylic acid esters via the Minisci homolytic alkoxycarbonylation of 5-halopyrimidines. The reaction was found to be highly regioselective, allowing the one-step synthesis of useful amounts (>10 g) of ethyl 5-bromopyrimidine-4-carboxylate where other methods proved difficult. Ethyl 5-bromopyrimidine-4-carboxylate was used for the preparation of potent CK2 inhibitors including CX-5011. This work represents an interesting application of radical chemistry for the preparation of pharmacologically active molecules.

  本文报告了通过 Minisci 均聚烷氧基羰基化 5-卤代嘧啶合成各种 5-卤代嘧啶-4-羧酸酯的过程。该反应具有很高的区域选择性，可以在其他方法难以合成的地方一步合成出有用量（大于 10 克）的 5-溴嘧啶-4-羧酸乙酯。5- 溴嘧啶-4-羧酸乙酯被用于制备包括 CX-5011 在内的强效 CK2 抑制剂。这项工作代表了自由基化学在制备药理活性分子方面的有趣应用。
• Structure-based design and synthesis of bicyclic fused-pyridines as MEK inhibitors
  作者：Hejun Lu、Wangyang Tu、Hongbo Fei、Guoji Xu、Qiyue Hu、Lei Zhang、Bing Lin、Jijun Yuan、Junzhao Yin、Aishen Gong、Mimi Wan、Dan Wang、Xiaoyan Zhu、Jun Feng、Qian Wang、Piaoyang Sun

  DOI：10.1016/j.bmcl.2014.03.086

  日期：2014.6

  The MAPK pathway is identified as one of the most important pathways involved in cell proliferation and differentiation. A key kinase in the pathway, the Mitogen-activated protein kinase kinase (MEK) is recognized as a promising target for antitumor drugs. Structure-based design and optimization of known MEK inhibitors resulted in identification of compound 10a as a potent non-ATP competitive MEK inhibitor in both in vitro and in vivo tests. (C) 2014 Elsevier Ltd. All rights reserved.
• [EN] REV-ERB AGONISTS FOR TH17-MEDIATED INFLAMMATORY DISORDERS<br/>[FR] AGONISTES REV-ERB POUR DES TROUBLES INFLAMMATOIRES À MÉDIATION PAR TH17
  申请人：[en]UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INCORPORATED

  公开号：WO2023122093A1

  公开（公告）日：2023-06-29

  The present disclosure provides compounds and their pharmaceutical compositions as selective agonists of REV-ERBα. The compounds are useful in various methods and uses, such as in the treatment of diseases including hyperglycemia, dyslipidemia, atherosclerosis, and autoimmune and inflammatory disorders or diseases, and as cancer therapeutics, such as for the treatment of glioblastoma, hepatocellular carcinoma, and colorectal cancer, and for immune-oncology purposes.