Methyl 3-butyl-1-methyl-5-nitro-2,6-dioxopyrimidine-4-carboxylate | 1072131-92-0

• 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: Methyl 3-butyl-1-methyl-5-nitro-2,6-dioxopyrimidine-4-carboxylate
• CAS: 1072131-92-0
• 化学式: C₁₁H₁₅N₃O₆
• 分子量: 285.257
• InChiKey: GXFUKJHGUAWBNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-butyl-1-methyl-5-nitro-2,6-dioxopyrimidine-4-carboxylate 在 溶剂黄146 、 锌 作用下， 生成
  参考文献：
  名称：

  Efficient and regioselective synthesis of pyrimido[5,4-d]pyrimidine-2,4,6,8(1H,3H,5H,7H)-tetraones with diversified substitutions

  摘要：

  A highly regioselective synthesis of N3-, N5-, and N7-substituted pyrimidopyrimidinetetraones is reported. The synthesis of N5-monosubstituted and N5-, N7-disubstituted compounds was achieved through selective alkylation and urea mediated pyrimidinedione formation reactions. For the more synthetically challenging N3-, N5-, and N7-trisubstituted structures, in combination with computational studies, a palladium catalyzed cascade reaction was successfully employed for the simultaneous formation of the pyrimidinedione ring and functionalization of the N3 position, which provided the trisubstituted products in high yields with full control of regioselectivity. By applying this methodology, key intermediate 26 was prepared in a few synthetic steps in good overall yield for further functionalization and quick SAR development. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.10.109
• 作为产物：
  描述：

  Methyl 3-butyl-1-methyl-2,6-dioxopyrimidine-4-carboxylate 在 硫酸 、 硝酸 作用下， 以84%的产率得到Methyl 3-butyl-1-methyl-5-nitro-2,6-dioxopyrimidine-4-carboxylate
  参考文献：
  名称：

  Efficient and regioselective synthesis of pyrimido[5,4-d]pyrimidine-2,4,6,8(1H,3H,5H,7H)-tetraones with diversified substitutions

  摘要：

  A highly regioselective synthesis of N3-, N5-, and N7-substituted pyrimidopyrimidinetetraones is reported. The synthesis of N5-monosubstituted and N5-, N7-disubstituted compounds was achieved through selective alkylation and urea mediated pyrimidinedione formation reactions. For the more synthetically challenging N3-, N5-, and N7-trisubstituted structures, in combination with computational studies, a palladium catalyzed cascade reaction was successfully employed for the simultaneous formation of the pyrimidinedione ring and functionalization of the N3 position, which provided the trisubstituted products in high yields with full control of regioselectivity. By applying this methodology, key intermediate 26 was prepared in a few synthetic steps in good overall yield for further functionalization and quick SAR development. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.10.109

文献信息

• WO2008/127591
  申请人：——

  公开号：——

  公开（公告）日：——
• PYRIMIDINEDIONE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Huang Xianhai

  公开号：US20100144764A1

  公开（公告）日：2010-06-10

  The present invention relates to Pyrimidinedione Derivatives, compositions comprising a Pyrimidinedione Derivative and methods for using the Pyrimidinedione Derivatives for treating or preventing a metabolic disorder, dyslipidemia, a cardiovascular disease, a neurological disorder, a hematological disease, cancer, inflammation, a respiratory disease, a gastroenterological disease, diabetes, a diabetic complication, obesity, an obesity-related disorder or non-alcoholic fatty liver disease.
• [EN] PYRIMIDINEDIONE DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE PYRIMIDINEDIONE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SCHERING CORP

  公开号：WO2008127591A2

  公开（公告）日：2008-10-23

  [EN] The present invention relates to Pyrimidinedione Derivatives, compositions comprising a Pyrimidinedione Derivative and methods for using the Pyrimidinedione Derivatives for treating or preventing a metabolic disorder, dyslipidemia, a cardiovascular disease, a neurological disorder, a hematological disease, cancer, inflammation, a respiratory disease, a gastroenterological disease, diabetes, a diabetic complicaton, obesity, an obesity-related disorder or non-alcoholic fatty liver disease.
  [FR] La présente invention concerne des dérivés de pyrimidinedione, des compositions comprenant un dérivé de pyrimidinedione et des procédés d'utilisation de dérivés de pyrimidinedione en vue du traitement ou de la prévention d'un trouble métabolique, d'une dyslipidémie, d'une maladie cardiovasculaire, d'une affection neurologique, d'une maladie hématologique, d'un cancer, d'une inflammation, d'une maladie respiratoire, d'une maladie gastro-entérologique, d'un diabète, d'une complication du diabète, d'une obésité, d'un trouble associé à l'obésité ou d'une stéatose hépatique non alcoolique.
• Efficient and regioselective synthesis of pyrimido[5,4-d]pyrimidine-2,4,6,8(1H,3H,5H,7H)-tetraones with diversified substitutions
  作者：Xianhai Huang、Nicolas Zorn、Anandan Palani、Robert Aslanian

  DOI：10.1016/j.tetlet.2012.10.109

  日期：2012.12

  A highly regioselective synthesis of N3-, N5-, and N7-substituted pyrimidopyrimidinetetraones is reported. The synthesis of N5-monosubstituted and N5-, N7-disubstituted compounds was achieved through selective alkylation and urea mediated pyrimidinedione formation reactions. For the more synthetically challenging N3-, N5-, and N7-trisubstituted structures, in combination with computational studies, a palladium catalyzed cascade reaction was successfully employed for the simultaneous formation of the pyrimidinedione ring and functionalization of the N3 position, which provided the trisubstituted products in high yields with full control of regioselectivity. By applying this methodology, key intermediate 26 was prepared in a few synthetic steps in good overall yield for further functionalization and quick SAR development. (C) 2012 Published by Elsevier Ltd.