2-amino-4,6-dimethoxy-5-thiocyanatopyrimidine | 1309567-37-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-4,6-dimethoxy-5-thiocyanatopyrimidine
• 英文别名: (2-Amino-4,6-dimethoxypyrimidin-5-yl) thiocyanate
• CAS: 1309567-37-0
• 化学式: C₇H₈N₄O₂S
• 分子量: 212.232
• InChiKey: NPMQNKUGJSUIMS-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  421.1±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-4,6-dimethoxy-5-thiocyanatopyrimidine 在 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-amino-5-(1-ethyl-1H-tetrazol-5-ylthio)-4,6-dimethoxypyrimidine
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of New Pyrimidine Derivatives Incorporating 1H-Tetrazol-5-ylthio Moiety

  摘要：

  In this study, some new 4,6-dimethoxy pyrimidine derivatives were synthesized. 2-Amino-4,6-dimethoxy-5-thiocyanatopyrimidine (2) was synthesized by a reaction of 2-amino-4,6-dimethoxypyrimidine with KSCN and was converted into 2-amino-5-(1H-tetrazol-5-ylthio)-4,6-dimethoxypyrimidine (4) by treatment with NaN3 in the presence of NH4Cl in DMF. Then, 1,5-disubstitute tetrazole compounds were obtained from 4 by the alkylation reaction. In addition, some 2-chloro-4,6-dimethoxy-5-substitute-pyrimidines were synthesized by the diazotization method. The structures of these compounds were established on the basis of IR, H-1 NMR, APT, and HRMS spectral data and were evaluated for antibacterial activities against various bacterial strains. The results showed that some of these compounds exhibited good antibacterial activity as that of standard antibiotics Penicillin, Ampicillin, and Erythromycin.

  DOI：

  10.1002/jhet.1585
• 作为产物：
  描述：

  硫氰酸铵 、 2-氨基-4,6-二甲氧基嘧啶 在 碘 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以70%的产率得到2-amino-4,6-dimethoxy-5-thiocyanatopyrimidine
  参考文献：
  名称：

  Iodine mediated an efficient and greener thiocyanation of aminopyrimidines by a modification of the Kaufmann’s reaction

  摘要：

  A new, safe, and efficient methodology for the thiocyanation of some aminopyrimidine derivatives has been implemented. The thiocyanation reactions proceeded at room temperature with high yields and selectivity. This route is a less toxic alternative to other common thiocyanation techniques because it uses molecular iodine as a halogen source, which is less reactive and easier to handle than chlorine or bromine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.058

文献信息

• Antimony(III) complexes with 2-amino-4,6-dimethoxypyrimidines: Synthesis, characterization and biological evaluation
  作者：Turgay Tunç、Mehmet Sayım Karacan、Hatice Ertabaklar、Musa Sarı、Nurcan Karacan、Orhan Büyükgüngör

  DOI：10.1016/j.jphotobiol.2015.09.022

  日期：2015.12

  6-dimethoxy-5-thiocyanatopyrimidine for the first time, and its structure was confirmed by X-ray crystallographic analysis. Novel binuclear antimony(III) compound of (3), Sb[5,5′-disulfanediylbis(2-amino-4,6-dimetoxypyrimidine)]Cl3}2 (4) and mononuclear antimony(III) compounds, SbL2Cl3, [L: 2-amino-5-thiol-4,6-dimethoxy pyrimidine (2) and 2-amino-5-(1H-tetrazol-5-ylthio)-4,6-dimethoxypyrimidine (6)] were

  通过首次还原2-氨基-4,6-二甲氧基-5-硫氰基嘧啶，合成了带有二硫键的新型嘧啶化合物5,5'-二硫代二基双（2-氨基-4,6-二甲氧基嘧啶）（3），通过X射线晶体学分析证实了其结构。（3）的新型双核锑（III）化合物，Sb [5,5'-二硫代二基双（2-氨基-4,6-二甲氧基嘧啶）] Cl 3 } 2（4）和单核锑（III）化合物，SbL 2 Cl 3，[L：2-氨基-5-硫醇-4,6-二甲氧基嘧啶（2）和2-氨基-5-（1H-四唑-5-基硫基）-4,6-二甲氧基嘧啶（6）]的合成和表征，借助元素分析，分子电导率，FT-IR，1 H-NMR和LC-MS技术。通过化合物的DFT / B3LYP / LANL2DZ方法优化的几何结构表明，单体化合物具有方形锥体形状。在体外测定了对热带利什曼原虫前鞭毛体的抗疟活性和谷胱甘肽还原酶抑制活性。结果表明（3）具有最佳的生物活性。