7-butyl-1,3-dipentyl-5H-pyrimido[5,4-d]pyrimidine-2,4,6,8-tetrone | 1415309-34-0

• 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: 7-butyl-1,3-dipentyl-5H-pyrimido[5,4-d]pyrimidine-2,4,6,8-tetrone
• CAS: 1415309-34-0
• 化学式: C₂₀H₃₂N₄O₄
• 分子量: 392.498
• InChiKey: WBIWBVSKINVXLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  90
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Methyl 2,6-dioxo-1,3-dipentylpyrimidine-4-carboxylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 N-碘代丁二酰亚胺 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 生成 7-butyl-1,3-dipentyl-5H-pyrimido[5,4-d]pyrimidine-2,4,6,8-tetrone
  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

• 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.