N-(5-(bromomethyl)-4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)pyrimidin-2-yl)-N-methylmethanesulfonamide | 1416000-55-9

• 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: N-(5-(bromomethyl)-4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)pyrimidin-2-yl)-N-methylmethanesulfonamide
• CAS: 1416000-55-9
• 化学式: C₁₆H₁₈Br₂FN₃O₂S
• 分子量: 495.21
• InChiKey: ZGRSXWFBCDYKLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  三丁基膦 、 N-(5-(bromomethyl)-4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)pyrimidin-2-yl)-N-methylmethanesulfonamide 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 tributyl[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-ylmethyl]phosphonium bromide 、
  参考文献：
  名称：

  Application of Flow Photochemical Bromination in the Synthesis of a 5-Bromomethylpyrimidine Precursor of Rosuvastatin: Improvement of Productivity and Product Purity

  摘要：

  In this report we present a flow photochemical bromination of a 5-methyl-substituted pyrimidine precursor of rosuvastatin. The study demonstrated that the reaction productivity can be increased markedly with a flow-mode approach compared to a batch-mode synthesis. Indeed, reaction times can be significantly shortened from a range of hours to a range of minutes. Moreover, in addition to process intensification, the study demonstrated that significantly lower overall levels of side products are obtained when photochemical bromination is conducted in a flow mode.

  DOI：

  10.1021/op300248y
• 作为产物：
  描述：

  N-[4-(4-氟苯基)-5-甲基-6-(1-甲基乙基)-2-嘧啶基]-N-甲基甲烷磺酰胺 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 15.0h， 以21%的产率得到N-(5-(bromomethyl)-4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)pyrimidin-2-yl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  Application of Flow Photochemical Bromination in the Synthesis of a 5-Bromomethylpyrimidine Precursor of Rosuvastatin: Improvement of Productivity and Product Purity

  摘要：

  In this report we present a flow photochemical bromination of a 5-methyl-substituted pyrimidine precursor of rosuvastatin. The study demonstrated that the reaction productivity can be increased markedly with a flow-mode approach compared to a batch-mode synthesis. Indeed, reaction times can be significantly shortened from a range of hours to a range of minutes. Moreover, in addition to process intensification, the study demonstrated that significantly lower overall levels of side products are obtained when photochemical bromination is conducted in a flow mode.

  DOI：

  10.1021/op300248y