N,N,3-trimethylimidazo[1,5-a]pyrazin-8-amine | 1040751-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1,5-a]吡嗪
• 英文名称: N,N,3-trimethylimidazo[1,5-a]pyrazin-8-amine
• CAS: 1040751-51-6
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: VJVFQFFAEBEQNM-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C (sublm)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N,3-trimethylimidazo[1,5-a]pyrazin-8-amine 、 对溴氟苯 在 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到5-(4-fluorophenyl)-N,N,3-trimethylimidazo[1,5-a]pyrazin-8-amine
  参考文献：
  名称：

  Palladium-Catalyzed Direct Heck Arylation of Dual π-Deficient/π-Excessive Heteroaromatics. Synthesis of C-5 Arylated Imidazo[1,5-a]pyrazines

  摘要：

  A general and efficient synthesis of 5-aryl imidazo[1,5-a]pyrazines by palladium-catalyzed coupling of the corresponding 8-substituted derivatives with aryl halides is described. The scope of this new reaction for the imidazo[1,5-a]pyrazine ring system was explored using three readily available 8-substituted precursors, X = NH2, NMe2, and OMe, as well as 8-aryl derivatives, X = Ar'. On the basis of these results as well as studies using a deuterated derivative, a Heck-like mechanism is proposed for this transformation.

  DOI：

  10.1021/ol800761r
• 作为产物：
  描述：

  二甲胺 、 8-chloro-3-methylimidazo[1,5-a]pyrazine 以 乙醇 为溶剂， 反应 8.0h， 以84%的产率得到N,N,3-trimethylimidazo[1,5-a]pyrazin-8-amine
  参考文献：
  名称：

  Palladium-Catalyzed Direct Heck Arylation of Dual π-Deficient/π-Excessive Heteroaromatics. Synthesis of C-5 Arylated Imidazo[1,5-a]pyrazines

  摘要：

  A general and efficient synthesis of 5-aryl imidazo[1,5-a]pyrazines by palladium-catalyzed coupling of the corresponding 8-substituted derivatives with aryl halides is described. The scope of this new reaction for the imidazo[1,5-a]pyrazine ring system was explored using three readily available 8-substituted precursors, X = NH2, NMe2, and OMe, as well as 8-aryl derivatives, X = Ar'. On the basis of these results as well as studies using a deuterated derivative, a Heck-like mechanism is proposed for this transformation.

  DOI：

  10.1021/ol800761r

文献信息

• Palladium-Catalyzed Direct Heck Arylation of Dual π-Deficient/π-Excessive Heteroaromatics. Synthesis of C-5 Arylated Imidazo[1,5-<i>a</i>]pyrazines
  作者：Jian-Xin Wang、J. Adam McCubbin、Meizhong Jin、Radoslaw S. Laufer、Yunyu Mao、Andrew P. Crew、Mark J. Mulvihill、Victor Snieckus

  DOI：10.1021/ol800761r

  日期：2008.7.17

  A general and efficient synthesis of 5-aryl imidazo[1,5-a]pyrazines by palladium-catalyzed coupling of the corresponding 8-substituted derivatives with aryl halides is described. The scope of this new reaction for the imidazo[1,5-a]pyrazine ring system was explored using three readily available 8-substituted precursors, X = NH2, NMe2, and OMe, as well as 8-aryl derivatives, X = Ar'. On the basis of these results as well as studies using a deuterated derivative, a Heck-like mechanism is proposed for this transformation.