5-bromo-2-hydroxypyrimidine | 154115-77-2

• 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: 5-bromo-2-hydroxypyrimidine
• 英文别名: 5-Bromo-1,2-dihydropyrimidin-2-one hydrochloride；5-bromo-1H-pyrimidin-2-one;hydrochloride
• CAS: 154115-77-2
• 化学式: C₄H₃BrN₂O*ClH
• 分子量: 211.446
• InChiKey: HWIYCPOXEBOZEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-2-hydroxypyrimidine 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以77%的产率得到5-溴-2-氯嘧啶
  参考文献：
  名称：

  Development of a Concise Scaleable Synthesis of 2-Chloro-5-(pyridin-2-yl) Pyrimidine via a Negishi Cross-Coupling

  摘要：

  A practical and scaleable synthesis of 2-chloro-5-(pyridin-2-yl) pyrimidine, an intermediate in the synthesis of a selective PDE-V inhibitor, was developed. A Negishi cross-coupling between the in situ prepared 2-pyridylzinc chloride and 5-iodo-2-chloropyrimidine catalyzed by Pd(PPh3)(4) afforded the product in one step. Development of a convenient purification did away with the necessity of chromatography, allowing the preparation of the product on kilogram scale.

  DOI：

  10.1021/op060241c
• 作为产物：
  描述：

  2-羟基嘧啶盐酸盐 在 盐酸 、 溴 作用下， 以 水 为溶剂， 以85%的产率得到5-bromo-2-hydroxypyrimidine
  参考文献：
  名称：

  Development of a Concise Scaleable Synthesis of 2-Chloro-5-(pyridin-2-yl) Pyrimidine via a Negishi Cross-Coupling

  摘要：

  A practical and scaleable synthesis of 2-chloro-5-(pyridin-2-yl) pyrimidine, an intermediate in the synthesis of a selective PDE-V inhibitor, was developed. A Negishi cross-coupling between the in situ prepared 2-pyridylzinc chloride and 5-iodo-2-chloropyrimidine catalyzed by Pd(PPh3)(4) afforded the product in one step. Development of a convenient purification did away with the necessity of chromatography, allowing the preparation of the product on kilogram scale.

  DOI：

  10.1021/op060241c