1,3-dimethyl-5-(N-ethylamino)pyrimidine-2,4-dione | 207112-20-7

• 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: 1,3-dimethyl-5-(N-ethylamino)pyrimidine-2,4-dione
• 英文别名: 5-(ethylamino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione；5-(Ethylamino)-1,3-dimethylpyrimidine-2,4-dione
• CAS: 207112-20-7
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: MQIHKMJVRYNEKP-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  276.0±43.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-(N-ethylamino)pyrimidine-2,4-dione 在 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 [5-Ethyl-1,3-dimethyl-6-[(2-methylphenoxy)methyl]-2,4-dioxopyrrolo[3,2-d]pyrimidin-7-yl]methyl 3-chlorobenzoate
  参考文献：
  名称：

  Studies on Pyrimidine-Annelated Heterocycles:  Synthesis of Pyrrolo[3,2-d]pyrimidines by Amine Oxide Rearrangement

  摘要：

  A number of pyrrolo[3,2-d]pyrimidine derivatives (5a-f) were synthesized in 90-95% yields from the corresponding 5-[N-[4-(aryloxy)but-2-ynyl]-N-ethylamino]-1,3-dimethyluracils 4a-f by simple treatment with 1 equiv of m-chloroperoxybenzoic acid in dichloromethane at 0-5 degrees C for 12-15 h. The resulting benzoates (5a-f) were easily converted to methoxy derivatives 11a-f in 92-94% yields when refluxed in methanol for 20-22 h.

  DOI：

  10.1021/jo9718861
• 作为产物：
  描述：

  1,3-二甲基-5-硝基尿嘧啶水合物 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1,3-dimethyl-5-(N-ethylamino)pyrimidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis of 1,3-dimethylpyrimidine-2,4-diones as potent and selective aldehyde dehydrogenase 1A1 (ALDH1A1) inhibitors with glucose consumption improving activity

  摘要：

  LDH1A1, one of 19 NAD(P)(+)-dependent aldehyde dehydrogenases, participates in multiple metabolic pathways and has been indicated to play an important role in obesity and diabetes. In this study, a series of 1,3-di-methylpyrimidine-2,4-diones were designed, synthesized and evaluated as novel selective aldehyde dehy-drogenase 1A1 inhibitors. Among them, compounds 46, 50, 53, 56 and 57 exhibited excellent inhibitory activity against ALDH1A1 with IC50 values in the low nanomolar range and high selectivity over ALDH1A2, ALDH1A3, ALDH2 and ALDH3A1. Furthermore, in vitro study demonstrated that compound 57 effectively improved glucose consumption in HepG2 cells compared to compound 1 (CM026).

  DOI：

  10.1016/j.bioorg.2020.103971

文献信息

• Facile Regioselective Synthesis of Functionalized Heterocycle-Tethered Spiro Compounds via an Intramolecular Electrophilic Ipso-Iodocyclization Process
  作者：K. Majumdar、Tapas Ghosh、Pranab Shyam

  DOI：10.1055/s-0031-1289526

  日期：2011.11

  A general, regioselective, and efficient intramolecular electrophilic ipso-iodocyclization of a series of N-alkyl-N-aryl phenylpropiolamides in the presence of I2 (molecular iodine) and NaHCO3 via 5-endo-dig mode of cyclization has been developed for the synthesis of hitherto unreported coumarin, quinolone, and pyrimidine-annelated heterocyclic compounds in excellent yields (84-92%). The development

  已经开发了在I 2（分子碘）和NaHCO 3存在下，通过5-内切-环化环化的方法，对一系列N-烷基-N-芳基苯基丙丙酰胺进行一般，区域选择性和有效的亲电子碘环化反应，用于迄今未报道的香豆素，喹诺酮和嘧啶退火的杂环化合物的合成，收率极高（84-92％）。该方法学的发展提供了高效温和的反应条件，可轻松分离产物。合成的螺衍生物为进一步的功能化和合成新的生物活性杂环提供了诱人和有用的范围。 azaspiro杂环-亲电ipso-碘环化-香豆素-喹诺酮-尿嘧啶
• Synthesis of benzodiazocine-annulated heterocycles by the implementation of Pd-catalyzed intramolecular Heck reaction
  作者：K.C. Majumdar、Krishanu Ray、Sintu Ganai

  DOI：10.1016/j.tetlet.2010.01.088

  日期：2010.3

  Synthesis of hitherto unreported benzodiazocine-annulated heterocycles by the implementation of palladium-catalyzed intramolecular Heck reaction has been achieved in excellent yields.

  通过钯催化的分子内Heck反应的实施，合成了迄今未报道的苯并二恶嗪环化的杂环，收率很高。
• Pd(OAc)₂-catalyzed dehydrogenative C–H activation: An expedient synthesis of uracil-annulated β-carbolinones
  作者：Biplab Mondal、Somjit Hazra、Tarun K Panda、Brindaban Roy

  DOI：10.3762/bjoc.11.146

  日期：——

  An intramolecular dehydrogenative C–H activation enabled an efficient synthesis of an uracil-annulated β-carbolinone ring system. The reaction is simple, efficient and high yielding (85–92%).

  一种分子内脱氢C-H活化反应使尿嘧啶环并β-咔唑酮环系统的合成变得高效。该反应简单、高效，产率高（85-92%）。
• Regioselective Synthesis of Pyrimidine‐Annulated Spiro Heterocycles by Radical Cyclization
  作者：K. C. Majumdar、T. K. Das、M. Jana

  DOI：10.1081/scc-200065003

  日期：2005.7

  Abstract The reaction of 5‐(2‐iodobenzamido)‐1,3‐dialkylpyrimidine‐2,4‐dione with Bu3SnH‐AIBN in refluxing benzene produces spiro‐heterocyclic compounds in 76–85% yield.

  摘要 5-(2-碘苯甲酰胺基)-1,3-二烷基嘧啶-2,4-二酮与 Bu3SnH-AIBN 在回流苯中反应生成螺杂环化合物，产率为 76-85%。
• Palladium-catalyzed intramolecular arylation of pyrimidines: a novel and expedient avenue to benzannulated pyridopyrimidines
  作者：K.C. Majumdar、B. Sinha、P.K. Maji、S.K. Chattopadhyay

  DOI：10.1016/j.tet.2009.01.107

  日期：2009.4

  A new efficient protocol for the synthesis of benzannulated pyrido[2,3-d]- and pyrido[3,2-d]pyrimidines has been successfully accomplished via the palladium-catalyzed intramolecular arylation of C–H bond of pyrimidine moiety. The methodology has also been extended to the synthesis of pyrimido[5,4,-c]isoquinoline-2,4,6(1H,3H,5H)-trione derivatives in excellent yields.

  通过钯催化嘧啶部分CH键的分子内芳基化反应，已成功完成了合成苯并吡啶并[2,3- d ]-和吡啶并[3,2- d ]嘧啶的新有效方法。该方法还扩展到以优异的产率合成嘧啶并[5,4，-c ]异喹啉-2,4,6（1 H，3 H，5 H）-三酮衍生物。