4,6-di(thiophen-2-yl)pyrimidin-2-ylamine | 82619-64-5

• 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: 4,6-di(thiophen-2-yl)pyrimidin-2-ylamine
• 英文别名: 2-amino-4,6-di(thiophen-2-yl)pyrimidine；4,6-Di(thiophen-2-yl)-2-aminopyrimidine；4,6-di(thiophen-2-yl)pyrimidin-2-amine；2-Amino-4,6-di-(2'-thienyl)pyrimidine；4,6-Bis(thiophen-2-yl)pyrimidin-2-amine；4,6-dithiophen-2-ylpyrimidin-2-amine
• CAS: 82619-64-5
• 化学式: C₁₂H₉N₃S₂
• 分子量: 259.356
• InChiKey: JKNVWCCCGBJZNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-di(thiophen-2-yl)pyrimidin-2-ylamine 在 Selectfluor 、 silver carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以51%的产率得到5-Fluoro-4,6-dithiophen-2-ylpyrimidin-2-amine
  参考文献：
  名称：

  Ag与Selectfluor联用对未保护的4,6-二取代的2-氨基嘧啶进行银辅助氟化

  摘要：

  提出了在Ag（I）存在下用Selectfluor对4，6-二取代的2-氨基嘧啶进行直接氟化，从而以可接受的高收率提供了相应的4，6-二取代的5-氟-2-氨基嘧啶。Ag（I）对于这种化学选择性氟化过程至关重要。讨论了4,6-二苯基5-氟-2-氨基嘧啶向N-（5-氟-4,6-二苯基嘧啶-2-基）-4-甲基苯磺酰胺的转化，并研究了其反应机理。

  DOI：

  10.1021/acs.joc.6b02624
• 作为产物：
  描述：

  在 双氧水 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以14.04 g的产率得到4,6-di(thiophen-2-yl)pyrimidin-2-ylamine
  参考文献：
  名称：

  Solution-phase parallel synthesis of 4,6-diaryl-pyrimidine-2-ylamines and 2-amino-5,5-disubstituted-3,5-dihydro-imidazol-4-ones via a rearrangement

  摘要：

  The reaction of chalcones and guanidine was investigated in the presence of an oxidizing agent. Depending on the order of the addition either a 4,6-diaryl-pyriniidine-2-ylamine or 2-aniino-5,5-disubstituted-3,5-dihydro-imidazol-4-one was obtained. The structures of the imidazolinones were elucidated by NMR spectroscopy and X-ray crystallography and for its formation a mechanism was proposed. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)01560-0

文献信息

• Heterocycles. Part I. A new route to the synthesis of substituted 2-aminopyrimidines
  作者：N. R. El-Rayyes

  DOI：10.1002/jhet.5570190240

  日期：1982.3

  Heterocyclic aldehydes (A) reacted with alkyl aryl ketones (B) to give the corresponding 1,3-diaryl-2-propen-1-ones (Ia-1). Condensation of these chalcones with guanidine produced the corresponding 2-amino-4,6-diarylpyrimidines (IIa-1). The structure of all products was substantiated by chemical and spectroscopic methods.

  杂环醛（A）与烷基芳基酮（B）反应，得到相应的1,3-二芳基-2-丙烯-1-酮（Ia-1）。这些查耳酮与胍的缩合产生相应的2-氨基-4,6-二芳基嘧啶（IIa-1）。所有产品的结构均通过化学和光谱法证实。
• Solution-phase parallel synthesis of 4,6-diaryl-pyrimidine-2-ylamines and 2-amino-5,5-disubstituted-3,5-dihydro-imidazol-4-ones via a rearrangement
  作者：László Varga、Tamás Nagy、István Kövesdi、Jordi Benet-Buchholz、György Dormán、László Ürge、Ferenc Darvas

  DOI：10.1016/s0040-4020(02)01560-0

  日期：2003.1

  The reaction of chalcones and guanidine was investigated in the presence of an oxidizing agent. Depending on the order of the addition either a 4,6-diaryl-pyriniidine-2-ylamine or 2-aniino-5,5-disubstituted-3,5-dihydro-imidazol-4-one was obtained. The structures of the imidazolinones were elucidated by NMR spectroscopy and X-ray crystallography and for its formation a mechanism was proposed. (C) 2003 Published by Elsevier Science Ltd.
• Pyrimidine Derivatives as Potent and Selective A₃ Adenosine Receptor Antagonists
  作者：Vicente Yaziji、David Rodríguez、Hugo Gutiérrez-de-Terán、Alberto Coelho、Olga Caamaño、Xerardo García-Mera、José Brea、María Isabel Loza、María Isabel Cadavid、Eddy Sotelo

  DOI：10.1021/jm100843z

  日期：2011.1.27

  Two regioisomeric series of diaryl 2- or 4-amidopyrimidines have been synthesized and their adenosine receptor affinities were determined in radioligand binding assays at the four human adenosine receptors (hARs). Some of the ligands prepared herein exhibit remarkable affinities (K-i < 10 nm) and, most noticeably, the absence of activity at the A(1), A(2A), and A(2B) receptors. The structural determinants that support the affinity and selectivity profiles of the series were highlighted through an integrated computational approach, combining a 3D-QSAR model built on the second generation of G Rid INdependent Descriptors (GRIND2) with a novel homology model of the hA(3) receptor. The robustness of the computational model was subsequently evaluated by the design of new derivatives exploring the alkyl substituent of the exocyclic amide group. The synthesis and evaluation of the novel compounds validated the predictive power of the model, exhibiting excellent agreement between predicted and experimental activities.
• EL-RAYYES, N. R., J. HETEROCYCL. CHEM., 1982, 19, N 2, 415-419
  作者：EL-RAYYES, N. R.

  DOI：——

  日期：——
• New pyrimidines incorporating thiophene and pyrrole moieties: synthesis and electrochemical polymerization
  作者：Anastasiya Yu. Bushueva、Elena V. Shklyaeva、Georgii G. Abashev

  DOI：10.1016/j.mencom.2009.11.012

  日期：2009.11

  The synthesis and electrochemical polymerization on the indium-tin oxide covered glass plates of two new substituted pyrimidines, namely, (1H-pyrrol-1-yl)-4,6-di(thiophen-2-yl)pyrimidine and [2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl]-4,6-di(thiophen-2-yl)-pyrimidine was performed; the structure of the latter was determined by X-ray methods.