Methyl 4-[3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyrimidin-2-yl]benzoate | 268737-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl 4-[3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyrimidin-2-yl]benzoate
• CAS: 268737-23-1
• 化学式: C₂₂H₂₈N₄O₂
• 分子量: 380.49
• InChiKey: UZGURWBGCDMNKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-[3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyrimidin-2-yl]benzoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以55%的产率得到4-(3-Amino-imidazo[1,2-a]pyrimidin-2-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  A novel dealkylation affording 3-aminoimidazo[1,2-a]pyridines: access to new substitution patterns by solid-phase synthesis

  摘要：

  The three-component synthesis of 5-aminoimidazo[1,2-a]pyridine derivatives has been extended by a novel acid-induced dealkyation reaction that removes the 1,1,3,3-tetramethylbutyl group derived from the isonitrile input. This reaction was conducted on the solid-phase using the HMBA linker and the resulting products subjected to reductive alkylation using several aldehydes, thereby accessing novel substitution patterns at the 3-position. (C) 2000 Elsevier Science Ltd.. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00003-4
• 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)- 、 1,1,3,3-四甲基丁基异腈 、 对甲酰基苯甲酸甲酯 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以35%的产率得到Methyl 4-[3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyrimidin-2-yl]benzoate
  参考文献：
  名称：

  A novel dealkylation affording 3-aminoimidazo[1,2-a]pyridines: access to new substitution patterns by solid-phase synthesis

  摘要：

  The three-component synthesis of 5-aminoimidazo[1,2-a]pyridine derivatives has been extended by a novel acid-induced dealkyation reaction that removes the 1,1,3,3-tetramethylbutyl group derived from the isonitrile input. This reaction was conducted on the solid-phase using the HMBA linker and the resulting products subjected to reductive alkylation using several aldehydes, thereby accessing novel substitution patterns at the 3-position. (C) 2000 Elsevier Science Ltd.. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00003-4

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。
• Re-evaluation of the outcome of a multiple component reaction—2- and 3-amino-imidazo[1,2-a]pyrimidines?
  作者：Gurjit S. Mandair、Mark Light、Andrea Russell、Mike Hursthouse、Mark Bradley

  DOI：10.1016/s0040-4039(02)00709-8

  日期：2002.6

  Multi-component reactions between aldehydes, isonitriles and 2-aminoazines do not always give the expected products. (C) 2002 Elsevier Science Ltd. All rights reserved.