4-methyl-6-(3-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester | 911856-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-methyl-6-(3-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester
• 英文别名: 3-O-tert-butyl 5-O-ethyl 6-methyl-4-(3-nitrophenyl)-2-pyrazol-1-yl-4H-pyrimidine-3,5-dicarboxylate
• CAS: 911856-99-0
• 化学式: C₂₂H₂₅N₅O₆
• 分子量: 455.47
• InChiKey: QZHQNIILRFWYPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-methyl-6-(3-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester 在 氨 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到2-amino-4-methyl-6-(3-nitrophenyl)-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m
• 作为产物：
  描述：

  间硝基苯甲醛 在 4-二甲氨基吡啶 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 60.0h， 生成 4-methyl-6-(3-nitrophenyl)-2-pyrazol-1-yl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m