ethyl 6-(bromomethyl)-1,2-dihydro-2-oxo-4-phenylpyrimidine-5-carboxylate

• 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: ethyl 6-(bromomethyl)-1,2-dihydro-2-oxo-4-phenylpyrimidine-5-carboxylate
• 英文别名: ethyl 6-bromomethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate；ethyl 6-bromomethyl-4-phenyl-pyrimidin-2(1H)-one-5-carboxylate；ethyl 6-(bromomethyl)-2-oxo-4-phenyl-1H-pyrimidine-5-carboxylate
• 化学式: C₁₄H₁₃BrN₂O₃
• 分子量: 337.173
• InChiKey: AKXHYSUOSQVFDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-(bromomethyl)-1,2-dihydro-2-oxo-4-phenylpyrimidine-5-carboxylate 、 一水合肼 以 乙醇 为溶剂， 反应 4.0h， 以71%的产率得到ethyl 6-hydrazinomethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A Convenient Route to New Pyrrolo[1,2-c]pyrimidone, Thiazolo[3,4-c]pyrimidone and Pyrimido[4,5-d]pyridazine Derivatives

  摘要：

  The utility of versatile, readily accessible ethyl 6-bromomethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate (3) and ethyl 6-bromomethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate (4) in the synthesis of some new pyrimidine, pyrimido[4,5-d]pyridazine, pyrrolo[1,2-c]pyrimidone and thiazolo[3,4-c]pyrimidone derivatives is reported.

  DOI：

  10.3987/com-08-11562
• 作为产物：
  描述：

  6-(溴甲基)-2-氧代-4-苯基-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以80%的产率得到ethyl 6-(bromomethyl)-1,2-dihydro-2-oxo-4-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

  摘要：

  Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation of DHPMs by CAN/AcOH at 80 degrees C. The reaction afforded a mixture of products while employing CAN in organic solvents without additives. However, the regioselective dehydrogenated product, ethyl 6-methyl-4-aryl(alkyl)-pyrimidin-2(1H)-one-5-carboxylate was obtained by performing the reaction with NaHCO3. The single crystal X-ray crystallography of ethyl 6-methyl-4-(2-phenyl)-pyrimidin-2(1H)-one-5-carboxylate revealed that the oxidized product existed in amidic form rather than aromatized enol form of pyrimidines. The efficiency of the present protocol enabled the synthesis of structurally diverse pyrimidines in moderate to good yields under milder reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.063

文献信息

• Synthesis and Antimicrobial Evaluation of Some New Pyrimidine Derivatives
  作者：Ahmad M. Farag、Nabila A. Kheder、Yahia N. Mabkhot

  DOI：10.3987/com-07-11286

  日期：——

  The utility of ethyl 6-methyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate (1) in the synthesis of some new pyrido[1,2-f]pyrimidine, pyrazolo-[3,4-b]pyrido[1,2-/]pyrimidine, 6-(4-substituted styryl)pyrimidine, pyrido[4,3-d]-pyrimidine, pynmido[5,4-d]pyridazine and substituted-6-(thien-2-yl)pyrimidine derivatives is reported. Antimicrobial evaluation of some selected examples from the synthesized

  6-甲基-2-氧代-4-苯基-1,2-二氢嘧啶-5-羧酸乙酯(1)在合成一些新的吡啶并[1,2-f]嘧啶、吡唑并-[3,4]中的应用-b]吡啶并[1,2-/]嘧啶、6-(4-取代苯乙烯基)嘧啶、吡啶并[4,3-d]-嘧啶、嘧啶并[5,4-d]哒嗪和取代-6-(噻吩报道了-2-基)嘧啶衍生物。对合成产物中的一些选定实例进行了抗菌评估。
• Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate
  作者：P. Shanmugam、P.T. Perumal

  DOI：10.1016/j.tet.2006.07.063

  日期：2006.10

  Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation of DHPMs by CAN/AcOH at 80 degrees C. The reaction afforded a mixture of products while employing CAN in organic solvents without additives. However, the regioselective dehydrogenated product, ethyl 6-methyl-4-aryl(alkyl)-pyrimidin-2(1H)-one-5-carboxylate was obtained by performing the reaction with NaHCO3. The single crystal X-ray crystallography of ethyl 6-methyl-4-(2-phenyl)-pyrimidin-2(1H)-one-5-carboxylate revealed that the oxidized product existed in amidic form rather than aromatized enol form of pyrimidines. The efficiency of the present protocol enabled the synthesis of structurally diverse pyrimidines in moderate to good yields under milder reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• A Convenient Route to New Pyrrolo[1,2-c]pyrimidone, Thiazolo[3,4-c]pyrimidone and Pyrimido[4,5-d]pyridazine Derivatives
  作者：Ahmad M. Farag、Nabila A. Kheder、Yahia N. Mabkhot

  DOI：10.3987/com-08-11562

  日期：——

  The utility of versatile, readily accessible ethyl 6-bromomethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate (3) and ethyl 6-bromomethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate (4) in the synthesis of some new pyrimidine, pyrimido[4,5-d]pyridazine, pyrrolo[1,2-c]pyrimidone and thiazolo[3,4-c]pyrimidone derivatives is reported.