6-[(2,6-difluorophenyl)fluoromethyl]-5-methylpyrimidine-2,4-(1H,3H)-dione | 1206190-44-4

• 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: 6-[(2,6-difluorophenyl)fluoromethyl]-5-methylpyrimidine-2,4-(1H,3H)-dione
• 英文别名: 6-[(2,6-difluorophenyl)-fluoromethyl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 1206190-44-4
• 化学式: C₁₂H₉F₃N₂O₂
• 分子量: 270.211
• InChiKey: COLQQJITZMZITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(烯丙氧基)甲氧基]-1-丙烯 、 6-[(2,6-difluorophenyl)fluoromethyl]-5-methylpyrimidine-2,4-(1H,3H)-dione 在 N,O-bis(trimethylsilyl)acetamide 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以76%的产率得到1-(allyloxymethyl)-6-[(2,6-difluorophenyl)fluoromethyl]-5-methylpyrimidine-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Prompt Lithiation of 1-Dimethylsulfamoylthymine Used for the Synthesis of 1-Allyloxymethyl-6-(α,2,6-trifluorobenzyl)thymine

  摘要：

  The 6-position of the uracil ring was activated for a lithiation reaction by condensing thymine with dimethylsulfamoyl chloride. X-ray crystallography was used to confirm the structure of the intermediate product 1-dimethylsulfamoylthymine, which was lithiated and subsequently treated with 2,6-difluorobenzaldehyde. The dimethylsulfamoyl group was removed by treatment with aq HCl and the alcohol was fluorinated with DAST. The fluoro-derivative was silylated and alkylated at the N1-position with bis(allyloxy)methane to give 1-allyloxymethyl-6-[(2,6-difluorophenyl)fluoromethyl]-5-methylpyrimidine-2,4(1H,3H)-dione, which showed moderate activity against HIV-1. An attempt was also made to activate 5-methyl-2-(methylthio)pyrimidin-4(3H)-one with dimethylsulfamoyl chloride for a lithiation reaction. However, X-ray crystallography and Subsequent reactions showed that the sulfamoylation had taken place on the oxygen at the 4-position.

  DOI：

  10.1055/s-0029-1216978
• 作为产物：
  描述：

  6-[(2,6-difluorophenyl)hydroxymethyl]-5-methylpyrimidine-2,4-(1H,3H)-dione 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到6-[(2,6-difluorophenyl)fluoromethyl]-5-methylpyrimidine-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Prompt Lithiation of 1-Dimethylsulfamoylthymine Used for the Synthesis of 1-Allyloxymethyl-6-(α,2,6-trifluorobenzyl)thymine

  摘要：

  The 6-position of the uracil ring was activated for a lithiation reaction by condensing thymine with dimethylsulfamoyl chloride. X-ray crystallography was used to confirm the structure of the intermediate product 1-dimethylsulfamoylthymine, which was lithiated and subsequently treated with 2,6-difluorobenzaldehyde. The dimethylsulfamoyl group was removed by treatment with aq HCl and the alcohol was fluorinated with DAST. The fluoro-derivative was silylated and alkylated at the N1-position with bis(allyloxy)methane to give 1-allyloxymethyl-6-[(2,6-difluorophenyl)fluoromethyl]-5-methylpyrimidine-2,4(1H,3H)-dione, which showed moderate activity against HIV-1. An attempt was also made to activate 5-methyl-2-(methylthio)pyrimidin-4(3H)-one with dimethylsulfamoyl chloride for a lithiation reaction. However, X-ray crystallography and Subsequent reactions showed that the sulfamoylation had taken place on the oxygen at the 4-position.

  DOI：

  10.1055/s-0029-1216978