N-(4-methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine | 112675-67-9

• 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-(4-methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine
• 英文别名: N-(4-methoxyphenyl)-4-pyridin-3-ylpyrimidin-2-amine
• CAS: 112675-67-9
• 化学式: C₁₆H₁₄N₄O
• 分子量: 278.313
• InChiKey: DUGLDJCYQADWEU-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C(Solv: ethanol (64-17-5))
• 沸点：
  509.0±60.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine 在 氩 、 水 、 乙醇 作用下， 以 氢溴酸 为溶剂， 反应 40.5h， 以giving 19.1 g of the desired product, mp 223°-225° C.的产率得到4-<<4-(3-pyridinyl)-2-pyrimidinyl>amino>phenol
  参考文献：
  名称：

  4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines

  摘要：

  本披露描述了具有抗哮喘活性的新型4,5,6-取代-N-(取代苯基)-2-嘧啶胺。

  公开号：

  US04788195A1
• 作为产物：
  描述：

  (E)-3-(二甲基氨基)-1-(吡啶-3-基)丙-2-烯-1-酮 生成 N-(4-methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine
  参考文献：
  名称：

  TORLEY, LAWRENCE W.;JOHNSON, BERNARD D.;DUSZA, JOHN P.

  摘要：

  DOI：

文献信息

• Synthesis of New N-Arylpyrimidin-2-amine Derivatives Using a Palladium Catalyst
  作者：Ibrahim El-Deeb、Jae Ryu、So Lee

  DOI：10.3390/molecules13040818

  日期：——

  New N-aryl-4-(pyridin-3-yl)pyrimidin-2-amine derivatives were synthesizedfrom the corresponding amines, applying optimized Buchwald-Hartwig aminationconditions using dichlorobis(triphenylphosphine)Pd(II), xantphos and sodium tertbutoxidein refluxing toluene under a nitrogen atmosphere. The target N-aryl derivativeswere obtained in moderate to good yields ranging from 27% to 82%. The proceduredescribed could be widely employed for the preparation of new heterocyclic compounds.The structures of the new compounds were confirmed by FT-NMR, FT-IR and elementalanalysis.

  通过应用优化的Buchwald-Hartwig氨基化条件，使用二氯双(三苯基膦)钯(II)、xantphos和叔丁醇钠，在氮气氛围下于回流甲苯中，从相应的胺合成了新型N-芳基-4-(吡啶-3-基)嘧啶-2-胺衍生物。所得到的N-芳基衍生物产率从中等到良好，范围在27%至82%之间。描述的程序可广泛用于制备新型杂环化合物。新化合物的结构通过FT-NMR、FT-IR和元素分析得到了确认。
• Cu/<i>N</i>,<i>N</i>′-Dibenzyloxalamide-Catalyzed <i>N</i>-Arylation of Heteroanilines
  作者：Zhixiang Chen、Dawei Ma

  DOI：10.1021/acs.orglett.9b02509

  日期：2019.9.6

  N,N'-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol % CuBr and 10 mol % DBO. For (hetero)aryl bromides/iodides, coupling reaction took place at 80-100 °C with 1 mol % CuI and 2 mol % DBO. A variety of heteroanilines worked well

  N，N'-二苄基草酰胺（DBO）被确定为一种强大的配体，用于促进Cu催化杂苯胺与（杂）芳基卤化物的偶联。对于（杂）芳基氯，偶联反应在130℃下与5mol％的CuBr和10mol％的DBO发生。对于（杂）芳基溴化物/碘化物，偶合反应在80-100°C下与1 mol％的CuI和2 mol％的DBO进行。各种杂苯胺效果很好，以高到极高的收率提供了芳基化产物。
• 4,5,6-Substituted-2-pyrimidinamines
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0233461A2

  公开（公告）日：1987-08-26

  This disclosure describes novel 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines having anti-asthmatic activity.

  本公开介绍了具有抗哮喘活性的新型 4,5,6-取代-N-（取代苯基）-2-嘧啶胺。
• Expedient Parallel Synthesis of 2-Amino-4-heteroarylpyrimidines
  作者：Matthew G. Bursavich、Sabrina Lombardi、Adam M. Gilbert

  DOI：10.1021/ol051339z

  日期：2005.9.1

  An expedient synthesis of diverse 2-amino-4-heteroarylpyrimidines via a 2-chloropyrimidine intermediate is described. A series of potentially biologically active analogues have been synthesized in two parallel steps to afford focused arrays.
• Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors
  作者：Rolf Paul、William A. Hallett、John W. Hanifin、Marvin F. Reich、Bernard D. Johnson、Robert H. Lenhard、John P. Dusza、Suresh S. Kerwar、Yang I Lin

  DOI：10.1021/jm00071a002

  日期：1993.9

  The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders. Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy. Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release. These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines. After examining a large number of analogs, N-[3-(1H-imidazol-1-yl)phenyl]-4-(2-pyridinyl)-2-pyrimidinamine (1-27) was chosen for toxicological evaluation.