7-(N,N-diethylamino)-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine | 74502-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-(N,N-diethylamino)-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine
• 英文别名: 7-(Diethylamino)-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine；N,N-diethyl-3-phenyltriazolo[4,5-d]pyrimidin-7-amine
• CAS: 74502-78-6
• 化学式: C₁₄H₁₆N₆
• 分子量: 268.321
• InChiKey: AHWKBIBDFQJPOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(N,N-diethylamino)-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine 在 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以69%的产率得到8-aza-6-diethylamino-9-(2-bromophenyl)purine
  参考文献：
  名称：

  Palladium‐Catalyzed N ³ ‐Directed C−H Halogenation of N ⁹ ‐Arylpurines and Azapurines

  摘要：

  AbstractA palladium‐catalyzed direct ortho‐halogenation of N9‐arylpurines was developed by using N‐halogenated succinimide (NBS/NCS/NIS) as the halogenation reagents. The current procedure offers a late‐stage strategy to generate N9‐(ortho‐haloaryl)purines in moderate to excellent yields. The protocol was applicable to the substrates with both electron‐rich and electron‐deficient substituents and only monohalogenated products were formed. Moreover, the purinyl N3‐atom was verified as the directing group to facilitate Pd‐catalyzed ortho‐C−H activation.

  DOI：

  10.1002/ejoc.202101266
• 作为产物：
  描述：

  7-chloro-3-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.28h， 生成 7-(N,N-diethylamino)-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine
  参考文献：
  名称：

  Higashino, Takeo; Katori, Tatsuhiko; Kawaraya, Hideji, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 337 - 343

  摘要：

  DOI：

文献信息

• Ring transformation of condensed pyrimidines by enamines and ynamines. Formation of condensed pyridines and condensed diazocines.
  作者：Akira MIYASHITA、Naokata TAIDO、Susumu SATO、Ken-ichi YAMAMOTO、Hitoshi ISHIDA、Takeo HIGASHINO

  DOI：10.1248/cpb.39.282

  日期：——

  A [4+2]-cycloaddition of quinazoline (2) and the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidine 4 with enamines 1a-e resulted in ring transformation into the quinolines, 3a and 3c, and the 3H-1, 2, 3-triazolo[4, 5-b]pyridines, 5a-e, respectively. Similarly, the ynamine 13a cycloadded to 2 and its 4-cyano derivative 6, giving the quinolines, 14a and 14b, respectively.On the other hand, the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidines 4, 15, 8, 16, 17, 18, and 19 underwent [2+2]-cycloaddition with the ynamine 13a, resulting in ring transformation into the corresponding 3H-1, 2, 3-triazolo[4, 5-d]-[1, 3]diazocines 21a-27. The 7-methoxy derivative 20, the 4-methoxy- and 4-cyano-1H-pyrazolo[3, 4-d]pyrimidines, 30 and 31, and the 6-cyano-9H-purine 36 also underwent [2+2]-cycloaddition with 13a to give the corresponding 3H-1, 2-3-triazolo[4, 5-b][1, 5]diazocine 28, 1H-pyrazolo[3, 4-b][1, 5]diazocines, 32 and 33, and 3H-imidazo[4, 5-b]-[1, 5]diazocine 37, respectively.The structures of the 1, 3- and 1, 5-diazocines, 21a and 28, were determined by X-ray crystallography.

  喹唑啉（2）和3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4）与烯胺（1a-e）进行[4+2]环加成反应，导致环转化为喹啉（3a和3c）和相应的3H-1, 2, 3-三氮杂[4, 5-b]吡啶（5a-e）。类似地，烯氨（13a）与2及其4-氰基衍生物6进行环加成，分别生成喹啉（14a和14b）。另一方面，3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4、15、8、16、17、18和19）与烯氨（13a）发生[2+2]环加成反应，导致环转化为相应的3H-1, 2, 3-三氮杂[4, 5-d]-[1, 3]二氮环（21a-27）。7-甲氧基衍生物20、4-甲氧基和4-氰基的1H-吡唑[3, 4-d]嘧啶（30和31）以及6-氰基-9H-嘌呤（36）也与13a发生[2+2]环加成，分别生成相应的3H-1, 2-3-三氮杂[4, 5-b][1, 5]二氮环（28）、1H-吡唑[3, 4-b][1, 5]二氮环（32和33）和3H-咪唑[4, 5-b]-[1, 5]二氮环（37）。1, 3-和1, 5-二氮环（21a和28）的结构通过X射线晶体学确定。
• Purinyl N³-Directed Palladium-Catalyzed C–H Alkoxylation of <i>N</i>⁹-Arylpurines: A Late-Stage Strategy to Synthesize <i>N</i>⁹-(<i>ortho</i>-Alkoxyl)arylpurines
  作者：Mingwu Yu、Zhiqian Wang、Miao Tian、Chenghu Lu、Shunlai Li、Hongguang Du

  DOI：10.1021/acs.joc.6b00148

  日期：2016.4.15

  A palladium-catalyzed alkoxylation of N-9-arylpurines with primary or secondary alcohols has been developed successfully, which is a rare C-H activation reaction of polynitrogenated purines and offers a late-stage strategy to synthesize N-9-(ortho-alkoxyl)-arylpurines. Although there are more than four nitrogen atoms present in the purine moiety, the reaction can be effectively conducted by sterically blocking the N-1 site for catalyst coordination and first employing the purinyl N-3 atom as a directing group.
• Higashino, Takeo; Katori, Tatsuhiko; Yoshida, Shizuo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 255 - 261
  作者：Higashino, Takeo、Katori, Tatsuhiko、Yoshida, Shizuo、Hayashi, Eisaku

  DOI：——

  日期：——
• HIGASHINO T.; KATORI T.; KAWARAYA H.; HAYASHI E., CHEM. AND PHARM. BULL., 1980, 28, NO 1, 337-343
  作者：HIGASHINO T.、 KATORI T.、 KAWARAYA H.、 HAYASHI E.

  DOI：——

  日期：——
• HIGASHINO TAKEO; KATORI TATSUHIKO; YOSHIDA SHIZUO; HAYASHI EISAKU, CHEM. AND PHARM. BULL., 1980, 28, NO 1, 255-261
  作者：HIGASHINO TAKEO、 KATORI TATSUHIKO、 YOSHIDA SHIZUO、 HAYASHI EISAKU

  DOI：——

  日期：——