2-phenyl-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyrimidin-3-amine | 1132764-28-3

• 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-phenyl-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyrimidin-3-amine
• 英文别名: 2-phenyl-N-(2-thiophen-2-ylethyl)imidazo[1,2-a]pyrimidin-3-amine
• CAS: 1132764-28-3
• 化学式: C₁₈H₁₆N₄S
• 分子量: 320.418
• InChiKey: VZLYYXDBISICDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 2-(噻吩-2-基)乙基异丁酯 、 苯甲醛 在 氯化锆(IV) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 以49%的产率得到2-phenyl-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyrimidin-3-amine
  参考文献：
  名称：

  Regioselective Synthesis of 3-Aminoimidazo[1,2-a]-pyrimidines under Continuous Flow Conditions

  摘要：

  Multicomponent synthesis of 3-aminoimidazo[1,2-a]pyrimidines usually affords a product mixture containing varying amounts of the corresponding 2-amino regioisomer. Modified methods, particularly microwave heating, have been employed to suppress formation of this side-product, but none of the revised protocols are readily amenable to scale. A continuous flow adaptation was found to offer improved regioselectivity toward the targeted 3-amino regioisomer with significantly shorter reaction times and also widened the scope of the reaction to permit the use of aliphatic aldehyde building blocks.

  DOI：

  10.1021/jo501861g

文献信息

• Regioselective, Solvent-Free Synthesis of 3-Aminoimidazo[1,2-<i>a</i>]pyrimidines Under Microwave Irradiation Promoted by Zeolite HY
  作者：Beining Chen、Mark Thompson、Jenny Hurst

  DOI：10.1055/s-0028-1087274

  日期：——

  Microwave-assisted, solvent-free condensation of 2-aminopyrimidine with aldehydes and isonitriles gave the desired 3-aminoimidazo[1,2-a]pyrimidine products with good to excellent regioselectivity. A hydrogen zeolite (‘zeolite HY’) was found to be a novel and effective promoter for the reaction, generally leading to clean conversion and also permitting use of the normally unreactive 4,6-dimethyl-2-aminopyrimidine.

  微波辅助无溶剂的2-氨基嘧啶与醛和异腈的缩合反应产生了所需的3-氨基咪唑[1,2-a]嘧啶产物，具有良好到优异的区域选择性。研究发现氢分子筛（‘分子筛HY’）是该反应的一种新颖且有效的促进剂，通常能实现干净的转化，并且允许使用通常不反应的4,6-二甲基-2-氨基嘧啶。