4-(3-methoxyphenyl)-6-phenylpyrimidin-2-amine | 1195977-36-6

• 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-(3-methoxyphenyl)-6-phenylpyrimidin-2-amine
• CAS: 1195977-36-6
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: PPFNUCVTMAKBJS-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C(Solv: ethanol (64-17-5); toluene (108-88-3))
• 沸点：
  517.3±42.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(3-methoxyphenyl)-6-phenylpyrimidin-2-amine 、 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 反应 0.1h， 以83%的产率得到N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4'-(m-methoxyphenyl)-6'-diphenylpyrimidin-2'-yl)thiourea
  参考文献：
  名称：

  Synthesis of N-tetra-O-acetyl-β-d-glucopyranosyl-N′-(4′,6′-diarylpyrimidin-2′-yl)thioureas

  摘要：

  Some 2-amino-4,6-diarylpyrimidines 2 have been prepared from substituted benzylideneacetophenones and guanidine hydrochloride in the presence of alkali by conventional heating in alcoholic medium and microwave heating in solvent-free conditions. N-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas 4 have been synthesized by reaction of per-O-acetylated glucopyranosyl isothiocyanate 1 and substituted 2-amino-4,6-diarylpyrimidines 2. Two different methods have been used, namely, refluxing in anhydrous dioxane and solvent-free microwave-assisted coupling. The second procedure afforded higher yields in much shorter reaction times. The compounds 2 and 4 were tested for their antibacterial and antifungal activities in vitro against Staphylococcus epidermidis, Enterobacter aerogenes and Candida albicans by disc diffusion method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.09.002
• 作为产物：
  描述：

  1-(3-methoxyphenyl)-3-phenyl-2-propene-1-one 、 胍 在 C₁₈H₁₁Cl₃FeN₄ 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以89%的产率得到4-(3-methoxyphenyl)-6-phenylpyrimidin-2-amine
  参考文献：
  名称：

  铁在空气中催化合成嘧啶

  摘要：

  在本文中，我们报道了在大气条件下醇催化的铁催化多组分脱氢官能化为嘧啶。使用具有明确的氧化还原非纯2-苯基偶氮（1,10-菲咯啉）配体的Fe（II）络合物作为催化剂，通过伯脱氢偶联制备了各种2,4,6-三取代的嘧啶空气中在100°C下与and形成的仲醇和仲醇。进行了一些对照实验，以了解并揭示合理的反应机理。

  DOI：

  10.1002/adsc.201901172

文献信息

• Iron-Catalyzed Alkyne-Based Multicomponent Synthesis of Pyrimidines under Air
  作者：Rakesh Mondal、Gargi Chakraborty、Amit Kumar Guin、Susmita Sarkar、Nanda D. Paul

  DOI：10.1021/acs.joc.1c00867

  日期：2021.10.1

  An iron-catalyzed sustainable, economically affordable, and eco-friendly synthetic protocol for the construction of various trisubstituted pyrimidines is described. A wide range of trisubstituted pyrimidines were prepared using a well-defined, easy to prepare, bench-stable, and phosphine-free iron catalyst featuring a redox-noninnocent tridentate arylazo pincer under comparatively mild aerobic conditions

  描述了一种用于构建各种三取代嘧啶的铁催化可持续、经济实惠且环保的合成方案。在相对温和的有氧条件下，通过醇与炔烃和脒的脱氢官能化，使用定义明确、易于制备、工作台稳定且不含膦的铁催化剂制备了各种三取代嘧啶.
• Metal-free cascade synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones
  作者：Xue Cui、Jianting Ma、Tingting Zeng、Junyu Xu、Youbin Li、Xuesong Wang

  DOI：10.1039/d1ra04319f

  日期：——

  metal-free synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones has been developed. In this procedure, various structural 2-aminopyrimidines, as well as 4,5-dihydroisoxazol-5-ols and pyrazoles were synthesized in moderate to excellent yields. A plausible mechanism was also proposed for the cascade reaction. This method represents an effective strategy towards the synthesis of unsymmetrical

  已经开发了一种方便的从咪唑烯胺酮合成不对称 2-氨基嘧啶的无金属方法。在此过程中，各种结构的 2-氨基嘧啶以及 4,5-二氢异恶唑-5-醇和吡唑以中等至优异的产率合成。还提出了级联反应的合理机制。该方法代表了一种合成不对称 2-氨基嘧啶的有效策略。
• Synthesis and spectral analysis of novel 3-(4,6-diarylpyrimidin-2-yl)-2-phenylthiazolidin-4-ones
  作者：M. Gopalakrishnan、J. Thanusu、V. Kanagarajan

  DOI：10.1007/s10593-010-0462-9

  日期：2009.12

  Novel 3-(4,6-diarylpyrimidin-2-yl)-2-phenylthiazolidin-4-ones are synthesized by the multicomponent cyclocondensation reaction of the appropriate 2-amino-4,6-diarylpyrimidines, benzaldehyde, and thioglycolic acid catalyzed by dicyclohexylcarbodiimide. The synthesized compounds have been characterized by melting point, elemental analysis, MS, FT-IR, H-1 and (13) NMR spectroscopic data.
• Synthesis of N-tetra-O-acetyl-β-d-glucopyranosyl-N′-(4′,6′-diarylpyrimidin-2′-yl)thioureas
  作者：Nguyen Dinh Thanh、Nguyen Thi Thanh Mai

  DOI：10.1016/j.carres.2009.09.002

  日期：2009.11

  Some 2-amino-4,6-diarylpyrimidines 2 have been prepared from substituted benzylideneacetophenones and guanidine hydrochloride in the presence of alkali by conventional heating in alcoholic medium and microwave heating in solvent-free conditions. N-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas 4 have been synthesized by reaction of per-O-acetylated glucopyranosyl isothiocyanate 1 and substituted 2-amino-4,6-diarylpyrimidines 2. Two different methods have been used, namely, refluxing in anhydrous dioxane and solvent-free microwave-assisted coupling. The second procedure afforded higher yields in much shorter reaction times. The compounds 2 and 4 were tested for their antibacterial and antifungal activities in vitro against Staphylococcus epidermidis, Enterobacter aerogenes and Candida albicans by disc diffusion method. (C) 2009 Elsevier Ltd. All rights reserved.
• Iron Catalyzed Synthesis of Pyrimidines Under Air
  作者：Rakesh Mondal、Suman Sinha、Siuli Das、Gargi Chakraborty、Nanda D. Paul

  DOI：10.1002/adsc.201901172

  日期：2020.2.6

  Herein we report an iron‐catalyzed multicomponent dehydrogenative functionalization of alcohols to pyrimidines under atmospheric conditions. Using a well‐defined Fe(II)‐complex featuring redox noninnocent 2‐phenylazo‐(1,10‐phenanthroline) ligand, as a catalyst, a wide array of 2,4,6‐trisubstituted pyrimidines were prepared via dehydrogenative coupling of primary and secondary alcohols with amidines

  在本文中，我们报道了在大气条件下醇催化的铁催化多组分脱氢官能化为嘧啶。使用具有明确的氧化还原非纯2-苯基偶氮（1,10-菲咯啉）配体的Fe（II）络合物作为催化剂，通过伯脱氢偶联制备了各种2,4,6-三取代的嘧啶空气中在100°C下与and形成的仲醇和仲醇。进行了一些对照实验，以了解并揭示合理的反应机理。