2-(benzylthio)-4-chloro-6-methylpyrimidine | 121180-58-3

• 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-(benzylthio)-4-chloro-6-methylpyrimidine
• 英文别名: 2-benzylthio-6-methyl-4-chloropyrimidine；Pyrimidine, 4-chloro-6-methyl-2-[(phenylmethyl)thio]-；2-benzylsulfanyl-4-chloro-6-methylpyrimidine
• CAS: 121180-58-3
• 化学式: C₁₂H₁₁ClN₂S
• mdl: MFCD01097750
• 分子量: 250.752
• InChiKey: ICSSORBMWQSROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzylthio)-4-chloro-6-methylpyrimidine 在 氨 作用下， 反应 24.0h， 以33%的产率得到2-benzylmercapto-6-methyl-pyrimidin-4-ylamine
  参考文献：
  名称：

  Pyrimidine Thioethers:  A Novel Class of HIV-1 Reverse Transcriptase Inhibitors with Activity Against BHAP-Resistant HIV

  摘要：

  A series of pyrimidine thioethers was synthesized and evaluated for inhibitory properties against wild-type HIV-1 reverse transcriptase (RT) and an RT carrying the resistance-conferring mutation P236L. Modifications of both the pyrimidine and the functionality attached through the thioether yielded several analogues, which demonstrated activity against both enzyme types, with IC50 values as low as 190 nM against wild-type and 66 nM against P236L RT. Evaluation of a select number of pyrimidine thioethers in cell culture showed that these compounds have excellent activity against HIV-1(IIIB)-WT and retain good activity against a laboratory-derived HIV-1(MF) delavirdine-resistant variant.

  DOI：

  10.1021/jm9800806
• 作为产物：
  描述：

  2-(benzylsulfanyl)-6-methylpyrimidin-4(3H)-one 在 三乙胺 、 三氯氧磷 作用下， 反应 0.17h， 以98%的产率得到2-(benzylthio)-4-chloro-6-methylpyrimidine
  参考文献：
  名称：

  Exploring the Scope for Scale-Up of Organic Chemistry Using a Large Batch Microwave Reactor

  摘要：

  A new batch microwave reactor has been evaluated in the context of palladium-mediated transformations, condensation reactions, nucleophilic aromatic substitution reactions, and alkylations. Importantly, a linear scaling approach was taken, no changes being made to the protocol when moving from the small, developmental scale to larger scales. In some cases reactions were scaled over 18,000-fold when moving from small (0.1-1 nmol) to large (1-18 mol) runs.

  DOI：

  10.1021/op900287j

文献信息

• Synthesis and antimicobacterial activity of 2-substituted 4-arylamino-6-methylpyrimidines
  作者：A. V. Erkin、V. I. Krutikov、E. B. Smirnova

  DOI：10.1134/s1070363208100216

  日期：2008.10

  2-Substituted 4-arylamino-6-methylpyrimidines were synthesized by stepwise modification of the structure of 6-methyl-2-thiouracyl through the intermediate 2-(ar)alkylthio-6-methyl-4-chloropyrimidines. Some of the compounds synthesized exhibit expressed antimycobacterial activity.
• GHONEIM, K. G.;EL-TELBANY, F. A.;EL-ENANY, M.;YOUSSEF, K., EGYPT. J. PHARM. SCI., 29,(1988) N-4, C. 169-178
  作者：GHONEIM, K. G.、EL-TELBANY, F. A.、EL-ENANY, M.、YOUSSEF, K.

  DOI：——

  日期：——
• Pyrimidine Thioethers:  A Novel Class of HIV-1 Reverse Transcriptase Inhibitors with Activity Against BHAP-Resistant HIV
  作者：Richard A. Nugent、Stephen T. Schlachter、Michael J. Murphy、Gary J. Cleek、Toni J. Poel、Donn G. Wishka、David R. Graber、Yoshihiko Yagi、Barbara J. Keiser、Robert A. Olmsted、Laurie A. Kopta、Steven M. Swaney、Susan M. Poppe、Joel Morris、W. Gary Tarpley、Richard C. Thomas

  DOI：10.1021/jm9800806

  日期：1998.9.1

  A series of pyrimidine thioethers was synthesized and evaluated for inhibitory properties against wild-type HIV-1 reverse transcriptase (RT) and an RT carrying the resistance-conferring mutation P236L. Modifications of both the pyrimidine and the functionality attached through the thioether yielded several analogues, which demonstrated activity against both enzyme types, with IC50 values as low as 190 nM against wild-type and 66 nM against P236L RT. Evaluation of a select number of pyrimidine thioethers in cell culture showed that these compounds have excellent activity against HIV-1(IIIB)-WT and retain good activity against a laboratory-derived HIV-1(MF) delavirdine-resistant variant.
• Exploring the Scope for Scale-Up of Organic Chemistry Using a Large Batch Microwave Reactor
  作者：Jason R. Schmink、Chad M. Kormos、William G. Devine、Nicholas E. Leadbeater

  DOI：10.1021/op900287j

  日期：2010.1.15

  A new batch microwave reactor has been evaluated in the context of palladium-mediated transformations, condensation reactions, nucleophilic aromatic substitution reactions, and alkylations. Importantly, a linear scaling approach was taken, no changes being made to the protocol when moving from the small, developmental scale to larger scales. In some cases reactions were scaled over 18,000-fold when moving from small (0.1-1 nmol) to large (1-18 mol) runs.