2,4-Diamino-6-(4-methoxyphenyl)pyrimidine-5-carbonitrile | 107199-97-3

• 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: 2,4-Diamino-6-(4-methoxyphenyl)pyrimidine-5-carbonitrile
• CAS: 107199-97-3
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: COIYTNINXSZMAN-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  604.7±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-Cyano-3-(4-methoxyphenyl)-3-morpholinoacrylonitrile 、 碳酸胍 以83%的产率得到2,4-Diamino-6-(4-methoxyphenyl)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Tominaga, Yoshinori; Matsuoka, Yoshiki; Oniyama, Yukio, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 647 - 660

  摘要：

  DOI：

文献信息

• A highly efficient synthesis of 2,4-diamino-6-arylpyrimidine-5-carbonitrile derivatives using NiCo2O4@Ni(BDC) metal-organic frameworks as a novel and bifunctional catalyst
  作者：Mohammad Ali Ghasemzadeh、Mina Azimi-Nasrabad、Simin Farhadi、Boshra Mirhosseini-Eshkevari

  DOI：10.1016/j.jorganchem.2019.120935

  日期：2019.11

  The NiCo2O4@Ni(BDC) metal-organic frameworks as a suitable and green catalyst have been developed for the one-pot synthesis of 2,4-diamino-6-arylpyrimidine-5-carbonitrile derivatives. The multi-component reactions of aldehydes, malononitrile and guanidine hydrochloride were efficiently catalyzed using a novel metal-organic framework under reflux conditions. Simple procedures, high yields, short reaction

  的镍钴2 ö 4 @Ni（BDC）的金属-有机骨架作为合适的和绿色的催化剂已经开发了用于在一锅合成2,4-二氨基-6-芳基嘧啶-5-甲腈衍生物。醛，丙二腈和盐酸胍的多组分反应使用新型金属有机骨架在回流条件下得到了有效催化。该程序的优点是操作简单，产率高，反应时间短和催化剂的可重复使用性。通过FT-IR，SEM，XRD，EDX，TGA，VSM和TEM分析对催化剂进行了全面表征。
• Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile promoted by amino-functionalized CoFe₂O₄@SiO₂ nanoparticles under conventional heating, microwave and ultrasound irradiations
  作者：Samaneh Barkhordarion-Mohammadi、Javad Safaei-Ghomi

  DOI：10.1515/znb-2017-0114

  日期：2018.1.26

  Amino-functionalized CoFe₂O₄@SiO₂ nanoparticles have been used as an efficient catalyst for the preparation of 2,4-diamino-6-arylpyrimidine-5-carbonitrile derivatives by the one-pot reaction of aromatic aldehydes, malononitrile, and guanidine hydrochloride under conventional heating, microwave, and ultrasound irradiations. This method provides several advantages including mild reaction conditions, the reusability of the catalyst and low catalyst loading, and the use of microwave and ultrasonic irradiation as a valuable and powerful tool.

  氨基功能化的CoFe₂O₄@SiO₂纳米颗粒已被用作高效催化剂，用于通过芳香醛、马来酰亚胺和盐酸胍的一锅法反应制备2,4-二氨基-6-芳基嘧啶-5-羧腈衍生物。该方法具有多种优点，包括温和的反应条件、催化剂的可重复使用和低催化剂负载量，以及微波和超声辐射作为宝贵而强大的工具。
• Nickel(II) Chromite Nanoparticles: An Eco-Friendly and Reusable Catalyst for Synthesis of 2,4-Diamino-6-aryl-pyrimidine-5-yl Cyanides under Ultrasonic Radiation
  作者：Bahareh Saeedi、Shahrzad Abdolmohammadi、Zohreh Mirjafary、Reza Kia-Kojoori

  DOI：10.2174/1386207323666200808180527

  日期：2021.3

  within short reaction times (15 min). All synthesized compounds were well characterized by IR, 1H and 13C NMR spectroscopy, and also by elemental analyses. Conclusion: In conclusion, a simple, efficient, and green synthesis of 2,4-diamino-6-arylpyrimidine- 5-yl cyanides was developed using NiCr2O4 NPs as a green nanocatalyst, and under ultrasound radiation as a green tool. The mild reaction conditions

  背景：绿色化学研究领域的主要因素之一是使用超声波作为一种多功能合成工具来驱动化学反应。此外，纳米结构的金属盐在化学反应中作为低成本、高效、多相和绿色的催化剂占有重要地位。嘧啶也具有重要意义，因为它是各种天然和非天然物质的核心结构，其中许多表现出多种生物活性和医学应用。 目的：本研究的目的是探索镍 (II) 铬铁矿纳米粒子 (NiCr 2 O 4 NPs) 作为绿色可回收催化剂在合成 2,4-二氨基-6-芳基嘧啶-5-基氰化物中的作用。在超声波辐射下。 方法：以NiCr 2 O 4 NPs为有效的多相催化剂，在室温条件下，在超声辐射下进行硝酸胍、芳香醛和丙二腈的直接环缩合反应，制备2,4-二氨基-6-芳基-嘧啶-5高产率的-基氰化物。根据简单的水热路线成功制备了所描述的催化剂，并通过 X 射线衍射 (XRD) 技术、色散能 X 射线 (EDS) 分析、扫描电子显微镜 (SEM) 和动态光散射
• Efficient and Facile Synthesis of 2,4-Diamino-6-arylpyrimidine-5-carbonitrile Under Solvent-Free Conditions
  作者：Liangce Rong、Hongxia Han、Lijiu Gao、Yisi Dai、Minxia Cao、Shujiang Tu

  DOI：10.1080/00397910902987784

  日期：2010.2.2

  An efficient and convenient method for the preparation of 2,4-diamino-6-arylpyrimidine-5-carbonitrile derivatives by the one-pot reaction of aromatic aldehydes, malononitrile, and guanidine carbonate, in the presence of sodium hydroxide under solvent-free conditions, was reported. This method has the advantages of excellent yields, mild reaction conditions, easy work up, and environmental friendliness over the existing procedures.
• Microwave-assisted one-pot synthesis of functionalized pyrimidines using ionic liquid
  作者：Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.1002/jhet.540

  日期：2011.5

  AbstractAn efficient one‐pot multicomponent synthesis of 2,4‐diamino‐5‐pyrimidinecarbonitrile derivatives has been achieved in excellent yields by the condensation of aromatic aldehydes, malononitrile, and guanidine using ionic liquid under controlled microwave irradiation (100 W) at 60°C. This green approach offers a number of advantages in terms of methodology, high‐product yield, short reaction time, mild reaction conditions, and easy workup. J. Heterocyclic Chem., (2011).