2,3-diamino-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one | 374078-08-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2,3-diamino-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one
• 英文别名: 2,3-diamino-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one；2,3-Diamino-5,6-dimethylthieno[2,3-d]pyrimidin-4-one
• CAS: 374078-08-7
• 化学式: C₈H₁₀N₄OS
• 分子量: 210.26
• InChiKey: DPLLKTRGSILWLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-diamino-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 1,6,7-trimethylthieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidin-8(3H)-one
  参考文献：
  名称：

  从双功能中间体合成新的噻吩并恶唑并嘧啶和噻吩并嘧啶四嗪衍生物

  摘要：

  由双功能中间体2,3-二氨基-5,6-二甲基噻吩并[2,3 - d ]嘧啶-4（3 H）-一衍生物13-17制备含有噻吩并恶唑并嘧啶和噻吩并嘧啶四嗪骨架的新化合物。还制备了2,3-二氢-3-取代的5,6-二甲基噻吩并[2,3 - d ]嘧啶-4（1 H）-一衍生物8-12。

  DOI：

  10.1002/jhet.5570380426
• 作为产物：
  描述：

  methyl 4,5-dimethyl-2-(1H-tetrazol-1-yl)-3-thiophenecarboxylate 在 一水合肼 作用下， 反应 7.0h， 以85%的产率得到2,3-diamino-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  由取代的2-（1 H-四唑-1-基）噻吩-3-羧酸烷基酯衍生的2,3-二氨基噻吩并[2,3- d ]嘧啶-4（3 H）-one的新便捷合成方法

  摘要：

  4,5-二取代和4-取代的烷基的2-氨基噻吩-3-羧酸酯与原甲酸三乙酯和叠氮化钠在乙酸，得到2-新反应（1 ħ -四唑-1-基）-4-R 1 - 5-R 2-噻吩衍生物。已经确定这些四唑与肼的反应产生了研究不足的2，3-二氨基噻吩并[2，3- d ]嘧啶-4（3H）-一系统。重要的是，上述反应是在肼作用下独特的四唑环裂解。

  DOI：

  10.1016/j.tet.2007.11.045

文献信息

• Understanding the tetrazole ring cleavage reaction with hydrazines: Structural determination and mechanistic insight
  作者：Olga Ya. Shyyka、Nazariy T. Pokhodylo、Yurii I. Slyvka、Evgeny A. Goreshnik、Mykola D. Obushak

  DOI：10.1016/j.tetlet.2018.02.016

  日期：2018.3

  N-nucleophiles in the recently developed one-pot method for pyrimidine core annulation via 1H-tetrazole ring cleavage was examined. The product structures, 2,3-diamino- or hydrazino derivatives of thieno[3,2-d]pyrimidin-4(3H)-ones, thieno[2,3-d]pyrimidin-4(3H)-ones and [1]benzofuro[3,2-d]pyrimidin-4(3H)-one, were elucidated based on NMR and single crystal X-ray analysis.

  在最近开发的通过1 H-四唑环裂解进行嘧啶核环化的一锅法中，研究了几种肼作为N-亲核试剂的行为的区别。噻吩并[3,2 - d ]嘧啶-4（3 H）-，噻吩并[2,3 - d ]嘧啶-4（3 H）-和基于NMR和单晶X射线分析，阐明了[1]苯并呋喃[3，2 - d ]嘧啶-4（3 H）-one。
• Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents
  作者：Hayam M. Ashour、Omaima G. Shaaban、Ola H. Rizk、Ibrahim M. El-Ashmawy

  DOI：10.1016/j.ejmech.2012.12.003

  日期：2013.4

  A new series of thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a] pyrimidines was synthesized. The newly synthesized compounds were evaluated for their anti-inflammatory and analgesic activity using diclofenac Na as a reference standard. Additionally, the ulcerogenic effects and acute toxicity (ALD(50)) values of the active compounds were also determined. In general, the thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine derivatives exhibited better biological activities than the thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines. Collectively, the thienotriazolopyrimidine derivatives 9, 13 and 14a were proved to display distinctive anti-inflammatory activity at the acute and subacute models as well as good analgesic profile with a delayed onset of action. Moreover, they revealed good gastrointestinal safety profile and are well tolerated by experimental animals with high safety margin (ALD(50) > 0.3 g/kg). (C) 2012 Elsevier Masson SAS. All rights reserved.
• New convenient synthesis of 2,3-diaminothieno[2,3-d]pyrimidin-4(3H)-one derivates from substituted alkyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylates
  作者：Nazariy T. Pokhodylo、Vasyl S. Matiychuk、Mykola D. Obushak

  DOI：10.1016/j.tet.2007.11.045

  日期：2008.2

  4,5-Disubstituted and 4-substituted alkyl 2-amino-thiophene-3-carboxylates react with triethyl orthoformate and sodium azide in acetic acid to yield new 2-(1H-tetrazol-1-yl)-4-R1-5-R2-thiophene derivates. It was established that the reaction of these tetrazoles with hydrazine generates the insufficiently studied 2,3-diaminothieno[2,3-d]pyrimidin-4(3H)-one system. It is significant that the reaction

  4,5-二取代和4-取代的烷基的2-氨基噻吩-3-羧酸酯与原甲酸三乙酯和叠氮化钠在乙酸，得到2-新反应（1 ħ -四唑-1-基）-4-R 1 - 5-R 2-噻吩衍生物。已经确定这些四唑与肼的反应产生了研究不足的2，3-二氨基噻吩并[2，3- d ]嘧啶-4（3H）-一系统。重要的是，上述反应是在肼作用下独特的四唑环裂解。
• Synthesis of new thienotriazolopyrimidine and thienopyrimidotetrazine derivatives from bifunctional intermediates
  作者：Maria Modica、Maria Santagati、Andrea Santagati

  DOI：10.1002/jhet.5570380426

  日期：2001.7

  New compounds containing the thienotriazolopyrimidine and thienopyrimidotetrazine skeleton are prepared from the bifunctional intermediates 2,3-diamino-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one derivatives 13–17. The 2,3-dihydro-3-substituted-5,6-dimethylthieno[2,3-d]pyrimidin-4(1H)-one derivatives 8–12 are also prepared.

  由双功能中间体2,3-二氨基-5,6-二甲基噻吩并[2,3 - d ]嘧啶-4（3 H）-一衍生物13-17制备含有噻吩并恶唑并嘧啶和噻吩并嘧啶四嗪骨架的新化合物。还制备了2,3-二氢-3-取代的5,6-二甲基噻吩并[2,3 - d ]嘧啶-4（1 H）-一衍生物8-12。