1,3,7-trimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,5-trione | 37587-44-3

• 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: 1,3,7-trimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,5-trione
• 英文别名: 5-hydroxy-1,3,7-trimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione；1,3,7-trimethyl-8H-pyrido[2,3-d]pyrimidine-2,4,5-trione
• CAS: 37587-44-3
• 化学式: C₁₀H₁₁N₃O₃
• 分子量: 221.216
• InChiKey: KIUOCKBEOITDTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 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：
  69.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3,7-trimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,5-trione 在 氢氧化钾 作用下， 反应 6.0h， 以69%的产率得到N,6-dimethyl-2-(methylamino)-4-oxo-1H-pyridine-3-carboxamide
  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
• 作为产物：
  描述：

  6-azido-1,3-dimethyluracil 在 溶剂黄146 、 三氟乙酸 作用下， 以 二苯醚 、 甲苯 为溶剂， 反应 7.5h， 生成 1,3,7-trimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,5-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

• Synthesis and biological activity of 8-alkyl(aryl)-6-cyanopyrido[2,3-d]-pyrimidine-2,4,5-triones
  作者：T. I. Skudarnova、O. A. Burova、N. M. Smirnova、G. M. Chelysheva、T. S. Safonova

  DOI：10.1007/bf02218996

  日期：1994.3

  diethylacetal of DNA and containing the methyl group at the position 7, contain the signal of the C(7)-CH 3 protons in the region of 2.30-2.76 ppm. With the object of synthesizing compounds containing the 6-pyridinecarboxylic acid fragment of the antibacterial preparations pipemidic and pyromidic acids [5, 6], the conditions of the hydrolysis of the 6-cyano derivatives (V)-(XII) in alkaline and acidic

  先前已经表明 [1-4] 1,3-二甲基-5-氰基乙酰基-6-氨基尿嘧啶 (I)-(VI) 在碱性或酸性介质中的杂环化导致 7-氨基或 7-羟基吡啶[ 2,3-d]嘧啶相应。为了分离出具有潜在抗菌活性的化合物，我们继续研究化合物（I）-（IV）的化学性质，并使用过量的试剂实现了它们与DMF和DMA的二乙缩醛的反应。由此获得6-氰基-8烷基(苄基，苯基)吡啶并[2,3-d]嘧啶-2,4,5-三酮(V)-(XII)。由尿嘧啶 (I)-(IV) 与 DMF 的二乙缩醛反应获得的化合物 (V)-(VIII) 的 PMR 光谱包含在 8.48 区域内的 C(7)-H 质子信号-8.60 ppm。吡啶并[2,3d]嘧啶(IX)-(XII)的PMR光谱，在 DNA 的二乙缩醛参与下合成并在第 7 位包含甲基，在 2.30-2.76 ppm 范围内包含 C(7)-CH 3 质子信号。为了合成含有抗菌制剂哌啶酸和吡咯酸
• 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.