1,3,6-Trimethyl-5-hydroxypyrido<2,3-d>pyrimidin-2,4,7(1,3,8H)-trione | 93738-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 1,3,6-Trimethyl-5-hydroxypyrido<2,3-d>pyrimidin-2,4,7(1,3,8H)-trione
• 英文别名: 1,3,6-trimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,5,7-tetraone；1.3.6-Trimethyl-5-hydroxy-pyrido<2.3-d>pyrimidin-2.4.7-1H.3H.8H-trion；5-hydroxy-1,3,6-trimethyl-8H-pyrido[2,3-d]pyrimidine-2,4,7-trione
• CAS: 93738-67-1
• 化学式: C₁₀H₁₁N₃O₄
• 分子量: 237.215
• InChiKey: VRDNDOZPDZYKIF-UHFFFAOYSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-azido-1,3-dimethyluracil 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二苯醚 为溶剂， 反应 1.67h， 生成 1,3,6-Trimethyl-5-hydroxypyrido<2,3-d>pyrimidin-2,4,7(1,3,8H)-trione
  参考文献：
  名称：

  Pyrido[2,3-d]pyrimidines, II. One step synthesis of pyrido[2,3-d]pyrimidines and pyrimido[4,5-b]quinolines from 6-amino uracils

  摘要：

  Reduction of 6-azidouracils 2 with hydrogen palladium or sodium dithionite afforded the corresponding 6-aminouracils 5 which could also be obtained by reaction of 2 with triphenylphosphane via phosphazenes and subsequent hydrolysis (Staudinger reaction). The use of trimethylphosphite instead of phosphanes yields with 2b the expected trimethoxyphosphazene 3c, whereas 2a reacts to the phosphonoaminopyrimidine 4. The syntheses of 5-hydroxy pyrido[2,3-d]pryimidine-2,4,7-triones 6, pyrido [2,3-d]pyrimidine-2,4,5-triones 8, cyclopenta[e]pyrido[2,3-d]pyrimidin-2,4,5-triones 7a, c, and tetrahydro-pyrimido[4,5-b]quinolin-2,4,5-triones 7b,d by condensation of 6-aminouracils 5 with malonates, ethylaceto/benzoylacetate, ethyl 2-oxocyclopentanecarboxylate and ethyl 2-oxocyclohexanecarboxylate, respectively, are described.

  DOI：

  10.1007/bf00807031

文献信息

• Time-Efficient Synthesis of Pyrido­[2,3-<i>d</i>]pyrimidinones via α-Oxoket­enes
  作者：Juan-Carlos Castillo、Jairo Quiroga、Jean Rodriguez、Yoann Coquerel

  DOI：10.1002/ejoc.201600171

  日期：2016.4

  intermediates generated in situ by microwave-assisted Wolff rearrangement of 2-diazo-1,3-dicarbonyl compounds have been found to react with 6-aminopyrimidine derivatives as 1,3-C,N-bis-nucleophiles to yield pyrido[2,3-d]pyrimidinones and related compounds amenable to further functionalization.

  已发现通过 2-重氮-1,3-二羰基化合物的微波辅助沃尔夫重排原位生成的 α-氧代烯酮反应中间体与 6-氨基嘧啶衍生物作为 1,3-C,N-双亲核试剂反应生成吡啶并[2,3-d]嘧啶酮和相关化合物可进一步官能化。
• Pyrido[2,3-d]pyrimidines, II. One step synthesis of pyrido[2,3-d]pyrimidines and pyrimido[4,5-b]quinolines from 6-amino uracils
  作者：A. F. Khattab、T. Kappe

  DOI：10.1007/bf00807031

  日期：——

  Reduction of 6-azidouracils 2 with hydrogen palladium or sodium dithionite afforded the corresponding 6-aminouracils 5 which could also be obtained by reaction of 2 with triphenylphosphane via phosphazenes and subsequent hydrolysis (Staudinger reaction). The use of trimethylphosphite instead of phosphanes yields with 2b the expected trimethoxyphosphazene 3c, whereas 2a reacts to the phosphonoaminopyrimidine 4. The syntheses of 5-hydroxy pyrido[2,3-d]pryimidine-2,4,7-triones 6, pyrido [2,3-d]pyrimidine-2,4,5-triones 8, cyclopenta[e]pyrido[2,3-d]pyrimidin-2,4,5-triones 7a, c, and tetrahydro-pyrimido[4,5-b]quinolin-2,4,5-triones 7b,d by condensation of 6-aminouracils 5 with malonates, ethylaceto/benzoylacetate, ethyl 2-oxocyclopentanecarboxylate and ethyl 2-oxocyclohexanecarboxylate, respectively, are described.