4-methoxy-6-phenylpyrimidin-2-ylamine | 36315-02-3

• 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: 4-methoxy-6-phenylpyrimidin-2-ylamine
• 英文别名: 2-amino-4-methoxy-6-phenylpyrimidine；4-methoxy-6-phenyl-pyrimidin-2-ylamine；2-Amino-4-methoxy-6-phenylpyrimidin；4-Methoxy-6-phenylpyrimidin-2-amine
• CAS: 36315-02-3
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: NVXGRADJIFIBIO-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C
• 沸点：
  425.5±37.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-6-phenylpyrimidin-2-ylamine 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以99%的产率得到2-amino-5-iodo-4-methoxy-6-phenylpyrimidine
  参考文献：
  名称：

  Structural studies on bioactive compounds. Part 29

  摘要：

  The immunological agent bropirimine 5 is a tetra-substituted pyrimidine with anticancer and interferon-inducing properties. Synthetic routes to novel 5-aryl analogues of bropirimine have been developed and their potential molecular recognition properties analysed by molecular modelling methods. Sterically challenged 2-amino-5-halo-6-phenylpyrimidin-4-ones (halo = Br or I) are poor substrates for palladium catalysed Suzuki cross-coupling reactions with benzeneboronic acid because the basic conditions of the reaction converts the amphoteric pyrimidinones to their unreactive enolic forms. Palladium-mediated reductive dehalogenation of the pyrimidinone substrates effectively competes with cross-coupling. 2-Amino-5-halo-4-methoxy-6-phenylpyrimidines can be converted to a range of 5-aryl derivatives with the 5-iodopyrimidines being the most efficient substrates. Hydrolysis of the 2-amino-5-aryl-4-methoxy-6-phenylpyrimidines affords the required pyrimidin-4-ones in high yields. Semi-empirical quantum mechanical calculations show how the nature of the 5-substituent influences the equilibrium between the 1H- and 3H-tautomeric forms, and the rotational freedom about the bond connecting the 6-phenyl group and the pyrimidine ring. Both of these factors may influence the biological properties of these compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00017-1
• 作为产物：
  描述：

  5-bromo-4-chloro-6-phenylpyrimidin-2-amine 在 palladium(II) acetate bis(diphenylphosphino)ferrocene potassium phosphate 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 22.5h， 生成 4-methoxy-6-phenylpyrimidin-2-ylamine
  参考文献：
  名称：

  Structural studies on bioactive compounds. Part 29

  摘要：

  The immunological agent bropirimine 5 is a tetra-substituted pyrimidine with anticancer and interferon-inducing properties. Synthetic routes to novel 5-aryl analogues of bropirimine have been developed and their potential molecular recognition properties analysed by molecular modelling methods. Sterically challenged 2-amino-5-halo-6-phenylpyrimidin-4-ones (halo = Br or I) are poor substrates for palladium catalysed Suzuki cross-coupling reactions with benzeneboronic acid because the basic conditions of the reaction converts the amphoteric pyrimidinones to their unreactive enolic forms. Palladium-mediated reductive dehalogenation of the pyrimidinone substrates effectively competes with cross-coupling. 2-Amino-5-halo-4-methoxy-6-phenylpyrimidines can be converted to a range of 5-aryl derivatives with the 5-iodopyrimidines being the most efficient substrates. Hydrolysis of the 2-amino-5-aryl-4-methoxy-6-phenylpyrimidines affords the required pyrimidin-4-ones in high yields. Semi-empirical quantum mechanical calculations show how the nature of the 5-substituent influences the equilibrium between the 1H- and 3H-tautomeric forms, and the rotational freedom about the bond connecting the 6-phenyl group and the pyrimidine ring. Both of these factors may influence the biological properties of these compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00017-1

文献信息

• A phase-switch purification approach for the expedient removal of tagged reagents and scavengers following their application in organic synthesis
  作者：Jason Siu、Ian R. Baxendale、Russell A. Lewthwaite、Steven V. Ley

  DOI：10.1039/b503778f

  日期：——

  In this paper we wish to report on a variety of expedient chemical transformations and purifications achieved via a generic ‘catch and release’ methodology, based on a synthetically inert bipyridyl chelating tag that can be selectively captured with a resin-bound copper(II) species. Utilising this approach we are able to derive many of the same benefits associated with both solid phase synthesis and supported reagent methods.

  本文旨在报道通过一种基于合成不活跃的双吡啶螯合标签的通用“捕获与释放”方法，实现的一系列便捷的化学转化和纯化。该方法可以选择性地利用树脂结合的铜(II)物种来捕获双吡啶螯合标签。采用这种方法，我们能够获得与固相合成和支持试剂法相关的许多相同益处。
• Novel Sulfonylurea Derivatives as Potential Antimicrobial Agents: Chemical Synthesis, Biological Evaluation, and Computational Study
  作者：Fan-Fei Meng、Ming-Hao Shang、Wei Wei、Zhen-Wu Yu、Jun-Lian Liu、Zheng-Ming Li、Zhong-Wen Wang、Jian-Guo Wang、Huan-Qin Dai

  DOI：10.3390/antibiotics12020323

  日期：——

  Staphylococcus aureus (MRSA) is a worldwide health threat and has already tormented humanity during its long history, creating an urgent need for the development of new classes of antibacterial agents. In this study, twenty-one novel sulfonylurea derivatives containing phenyl-5-vinyl and pyrimidinyl-4-aryl moieties were designed and synthesized, among which, nine compounds exhibited inhibitory potencies against

  耐甲氧西林金黄色葡萄球菌 (MRSA) 是一种全球性的健康威胁，在其悠久的历史中已经折磨着人类，因此迫切需要开发新型抗菌剂。本研究设计并合成了 21 种含有苯基-5-乙烯基和嘧啶基-4-芳基部分的新型磺酰脲类衍生物，其中 9 种化合物对革兰氏阳性菌具有抑制作用：MRSA（朝阳临床分离株）、金黄色葡萄球菌 ATCC6538、耐万古霉素肠球菌 309 (VRE-309) 和枯草芽孢杆菌 ATCC 6633。尤其是，9i 和 9q 对四种细菌菌株表现出抑制活性，最低抑菌浓度 (MIC) 为 0.78-1.56 μg/mL ，以及相当多的其他 MRSA 临床菌株，MIC 为 0.78 μg/mL，优于阳性对照万古霉素（MIC 为 1 μg/mL）和甲氧西林（MIC >200 μg/mL）。这是磺酰脲类衍生物首次被确定为针对不同 MRSA 临床分离株的有希望的抑制剂。此外，所有合成化合物对白色念珠菌的