2-methyl-6-cyano-9-(4-methylphenyl)-9H-purine | 1187085-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-6-cyano-9-(4-methylphenyl)-9H-purine
• 英文别名: 2-Methyl-9-(4-methylphenyl)purine-6-carbonitrile；2-methyl-9-(4-methylphenyl)purine-6-carbonitrile
• CAS: 1187085-98-8
• 化学式: C₁₄H₁₁N₅
• 分子量: 249.275
• InChiKey: FRTNRQOKMHOZIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-6-cyano-9-(4-methylphenyl)-9H-purine 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以61%的产率得到6-methyl-9-(4-methylphenyl)-9H-purine-6-carboximidamide
  参考文献：
  名称：

  Reactions of 9-Aryl-6-cyanopurines with Primary Amines

  摘要：

  Two structural isomers (9-aryl-6-cyanopurines and imidazole-4,5-dicarbonitriles) were isolated from the reaction of (Z)-Nl-aryl-N2-(2-amino-l,2-dicyanovinyl)formamidines with triethyl orthoacetate or propionate. On the other hand, 9-aryl-6-cyanopurines were the only product, when triethyl orthoformate was used. The reaction of 9-aryl-6-cyanopurines with hydroxylamine hydrochloride in dichloromethane/ethanol at room temperature furnished 6-amidinopurines, while reaction with primary amines afforded pyrimido[5,4-d]pyrimidines. In addition, 9-aryl-6-cyanopurines reacted with hydrazine monohydrate under mild conditions to give 4-imino-N8-arylpyrimido[5,4-d]pyrimidines. The latter furnished novel pyrimido[4,5-e][1,2,4]triazolo[1,5-c]pyrimidines when refluxed with an excess of triethyl orthoesters. The new compounds were fully characterized and single crystal X-ray analyses have been carried out on 9-(4-methoxyphenyl)-9H-purine-6-carboximidamide and 2-methyl1-[(E)-p-tolyliminomethyl]-1H-imidazole-4,5-dicarbonitrile.

  DOI：

  10.3987/com-09-11713
• 作为产物：
  描述：

  原乙酸三乙酯 、 (Z)-N-(2-amino-1,2-dicyanovinyl)-N'-p-tolylformamidine 反应 2.0h， 以25%的产率得到2-methyl-6-cyano-9-(4-methylphenyl)-9H-purine
  参考文献：
  名称：

  Reactions of 9-Aryl-6-cyanopurines with Primary Amines

  摘要：

  Two structural isomers (9-aryl-6-cyanopurines and imidazole-4,5-dicarbonitriles) were isolated from the reaction of (Z)-Nl-aryl-N2-(2-amino-l,2-dicyanovinyl)formamidines with triethyl orthoacetate or propionate. On the other hand, 9-aryl-6-cyanopurines were the only product, when triethyl orthoformate was used. The reaction of 9-aryl-6-cyanopurines with hydroxylamine hydrochloride in dichloromethane/ethanol at room temperature furnished 6-amidinopurines, while reaction with primary amines afforded pyrimido[5,4-d]pyrimidines. In addition, 9-aryl-6-cyanopurines reacted with hydrazine monohydrate under mild conditions to give 4-imino-N8-arylpyrimido[5,4-d]pyrimidines. The latter furnished novel pyrimido[4,5-e][1,2,4]triazolo[1,5-c]pyrimidines when refluxed with an excess of triethyl orthoesters. The new compounds were fully characterized and single crystal X-ray analyses have been carried out on 9-(4-methoxyphenyl)-9H-purine-6-carboximidamide and 2-methyl1-[(E)-p-tolyliminomethyl]-1H-imidazole-4,5-dicarbonitrile.

  DOI：

  10.3987/com-09-11713