(4-hydroxy-6-phenyl-2-pyrimidynyl)cyanamide | 6112-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4-hydroxy-6-phenyl-2-pyrimidynyl)cyanamide
• 英文别名: N-[(4-hydroxy-6-phenyl)pyrimidin-2-yl]cyanamide；(6-Oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)cyanamide；(6-oxo-4-phenyl-1H-pyrimidin-2-yl)cyanamide
• CAS: 6112-68-1
• 化学式: C₁₁H₈N₄O
• 分子量: 212.211
• InChiKey: HJIOANBIHWDTJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-hydroxy-6-phenyl-2-pyrimidynyl)cyanamide 在 盐酸 、 三氯氧磷 作用下， 以 乙二醇乙醚 为溶剂， 反应 25.5h， 生成 5,6-dichloro-N-<4-chloro-6-phenyl-2-pyrimidinyl>-1H-benzimidazol-2-amine
  参考文献：
  名称：

  N2-1H-Benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines as potential antifilarial agents

  摘要：

  A series of N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI) was synthesized for antifilarial evaluation. Condensation of the requisite beta-keto ester (VI) with N-cyanoguanidine afforded 2-pyrimidinylcyanamides (VIIa,b) and (5,6,7,8-tetrahydro-4-hydroxy-2-quinazolinyl)cyanamide (VIIc). Reaction of VII with a substituted o-phenylenediamine gave 2-(1H-benzimidazol-2-ylamino)-4-pyrimidinols and 2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-5,6,7, 8-tetrahydro-4-quinazolinol (IX). Chlorination with phosphoryl chloride, followed by condensation with the appropriate substituted benzenamine, gave the desired N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI). None of these compounds possessed antifilarial activity against Litomosoides carinii or Brugia pahangi infections in jirds.

  DOI：

  10.1021/jm00363a017
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 二聚氰胺 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 144.0h， 以34%的产率得到(4-hydroxy-6-phenyl-2-pyrimidynyl)cyanamide
  参考文献：
  名称：

  N2-1H-Benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines as potential antifilarial agents

  摘要：

  A series of N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI) was synthesized for antifilarial evaluation. Condensation of the requisite beta-keto ester (VI) with N-cyanoguanidine afforded 2-pyrimidinylcyanamides (VIIa,b) and (5,6,7,8-tetrahydro-4-hydroxy-2-quinazolinyl)cyanamide (VIIc). Reaction of VII with a substituted o-phenylenediamine gave 2-(1H-benzimidazol-2-ylamino)-4-pyrimidinols and 2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-5,6,7, 8-tetrahydro-4-quinazolinol (IX). Chlorination with phosphoryl chloride, followed by condensation with the appropriate substituted benzenamine, gave the desired N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI). None of these compounds possessed antifilarial activity against Litomosoides carinii or Brugia pahangi infections in jirds.

  DOI：

  10.1021/jm00363a017

文献信息

• An efficient synthesis of 2,4,7-trisubstituted pyrimido[1,2-a][1,3,5]triazin-6-ones
  作者：Nikhil Sachdeva、Anton V. Dolzhenko、Seow Joo Lim、Wee Ling Ong、Wai Keung Chui

  DOI：10.1039/c5nj00405e

  日期：——

  5]triazin-6-one scaffold was successfully achieved by the introduction of substituents into positions 2 and 7 via two complementary approaches for the synthesis of key intermediates viz. pyrimidinylguanidines. Variations in position 4 of the pyrimido[1,2-a][1,3,5]triazine ring were made available by the regioselective introduction of various substituents via the triazine ring closure with corresponding aldehydes

  开发了一种制备在环的2、4和7位官能化的新型嘧啶并[1,2- a ] [1,3,5]三嗪-6-衍生物的方法。嘧啶并[1,2- a ] [1,3,5]三嗪-6-一个骨架的衍生化多样性是通过两种互补方法将取代基引入位置2和7来合成关键中间体而成功实现的即 嘧啶基胍。嘧啶并[1,2- a ] [1,3,5]三嗪环第4位的变化可通过以下方法实现：三嗪与相应的醛一起闭环。该方法的范围通过制备66个嘧啶并[1,2- a ] [1,3,5] triazin-6- one的文库进行了说明，事实证明该文库是新的选择性抗癌药的来源。还研究了所制备化合物的互变异构偏好性和抗癌特性。
• An efficient microwave assisted synthesis of N′-aryl/(alkyl)-substituted N-(4-hydroxy-6-phenylpyrimidin-2-yl)guanidines: Scope and limitations
  作者：Paulo A. Machicao、Scott R. Burt、Ryan K. Christensen、Nathan B. Lohner、J.D. Singleton、Matt A. Peterson

  DOI：10.1016/j.tetlet.2017.03.063

  日期：2017.6

  Treatment of N-[(4-hydroxy-6-phenyl)pyrimidin-2-yl]cyanamide with 1° alkyl or arylamines in isopropyl alcohol for only 10 min at 110–120 °C under microwave conditions gave the corresponding N′-alkyl(aryl)guanidine derivatives in excellent yields (65–84%). Isolated yields were greatest when >1.0 equiv. of amines were employed, but excellent results were also obtained when aryl and alkylamines were reacted

  在微波条件下，在110-120°C的条件下，在异丙醇中用1°烷基或芳基胺对N-[（4-羟基-6-苯基）嘧啶-2-基]氰酰胺进行处理仅10分钟，得到相应的N'-烷基（芳基）胍衍生物的产率极高（65-84％）。大于1.0当量时，孤立的产量最高。使用芳族胺，但是当芳基胺和烷基胺以更高的原子经济负荷（1.0当量；分别为70％和72％的产率）反应时，也获得了优异的结果。具有高吸电子取代基（例如CO 2）的芳胺H）或缺乏pi的杂环（例如各种取代的氨基吡啶）在这些条件下不能很好地起作用，并且与尿素和/或氨基酸的反应没有得到可检测的产物。处理非常简单，只需在烧结玻璃漏斗中收集和清洗产品即可。获得的产品均为分析纯形式，大约需要1个小时才能制备，开始精加工。
• Pohl, Journal fur praktische Chemie (Leipzig 1954), 1908, vol. <2> 77, p. 542
  作者：Pohl

  DOI：——

  日期：——
• REMBARZ, G.;FISCHER, E.;JAKUBOWSKI, S.;EVERS, R., WISS. Z. WILCHELM-PIECK-UNIV. ROSTOCK. NATURWISS. R., 1982, 31, N 9, 11-1+
  作者：REMBARZ, G.、FISCHER, E.、JAKUBOWSKI, S.、EVERS, R.

  DOI：——

  日期：——