2,4-diamino-6-(4-chlorophenyl)-5-pyrimidinecarbonitrile | 99973-69-0

• 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-chlorophenyl)-5-pyrimidinecarbonitrile
• 英文别名: 2,4-diamino-6-(4-chlorophenyl)pyrimidine-5-carbonitrile；2,4-diamino-6-(4-chloro-phenyl)-pyrimidine-5-carbonitrile；2,4-Diamino-6-(4-chlor-phenyl)-pyrimidin-5-carbonitril
• CAS: 99973-69-0
• 化学式: C₁₁H₈ClN₅
• 分子量: 245.671
• InChiKey: LLSPDPUYMFGAEE-UHFFFAOYSA-N

物化性质

• 熔点：
  229-231 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  605.2±65.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 在 bismuth (III) nitrate pentahydrate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.07h， 生成 2,4-diamino-6-(4-chlorophenyl)-5-pyrimidinecarbonitrile
  参考文献：
  名称：

  在Bi（NO 3）3·5H 2 O作为温和高效的催化剂存在下快速嘧啶和嘧啶酮衍生物的三组分合成

  摘要：

  硝酸铋（III）五水合物被发现是一种温和高效的催化剂，可通过醛，N-未取代的idine，丙二腈或氰基乙酸乙酯的三组分反应快速合成4-氨基-5-嘧啶腈和嘧啶酮衍生物。水热条件。该反应方案是快速且简单的，随后以高纯度至优良产率形成相应的嘧啶和嘧啶酮衍生物。

  DOI：

  10.1007/s11164-013-1172-6

文献信息

• Facile Synthesis of Some Novel Tetrasubstituted 2,4-Diaminopyrimidine Derivatives in Aqueous Glucose Solution as a Fully Green Medium and Promoter
  作者：Reza Aryan、Hamid Beyzaei、Fatemeh Sadeghi

  DOI：10.1002/jhet.2514

  日期：2016.11

  A novel environmentally benign method toward the synthesis of some novel tetrasubstituted 2,4‐diaminopyrimidine derivatives using an aqueous glucose‐mediated one‐pot three‐component reaction of malononitrile with various benzaldehyde and amidine derivatives is reported. Some pyrimidine derivatives possessing α‐amino acid moiety were synthesized by the present protocol for the first time. This protocol

  报道了一种新的环境友好的方法，该方法利用丙二酸与各种苯甲醛和am衍生物的葡萄糖水溶液一锅三组分反应合成一些新颖的四取代的2,4-二氨基嘧啶衍生物。通过本方案首次合成了一些具有α-氨基酸部分的嘧啶衍生物。该方案具有以下优势：反应条件简单，使用天然存在的葡萄糖作为促进剂，以水作为溶剂，后处理简单，反应时间相对较短，产品收率高。
• 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。
• Granulated copper oxide nanocatalyst: a mild and efficient reusable catalyst for the one-pot synthesis of 4-amino-5-pyrimidinecarbonitriles under aqueous conditions
  作者：Seyed Javad Ahmadi、Sodeh Sadjadi、Morteza Hosseinpour

  DOI：10.1007/s00706-011-0579-2

  日期：2011.11

  An efficient method for the synthesis of 4-amino-5-pyrimidinecarbonitriles by the three-component reaction of malononitrile, aldehydes, and N-unsubstituted amidines under aqueous conditions using CuO microspheres as catalyst is reported. The catalyst exhibited remarkable reusable activity.
• Three-Component Synthesis of Pyrimidine and Pyrimidinone Derivatives in the Presence of High-Surface-Area MgO, a Highly Effective Heterogeneous Base Catalyst
  作者：Hassan Sheibani、Mohammad Seifi、Ayoob Bazgir

  DOI：10.1080/00397910802474982

  日期：2009.2.25

  Magnesium oxide (MgO) effectively catalyzes the three-component reaction of aldehydes, amidine systems, and malononitrile or ethyl cyanoacetate to form 4-amino-5-pyrimidine carbonitrile and pyrimidinone derivatives, respectively. The salient features of this method include high conversions, short reaction times, cleaner reaction profiles, and the use of inexpensive and readily available catalyst.