2,4-dimethoxy-6-(3-hydroxypropyl)-5-methylpyrimidine | 156569-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dimethoxy-6-(3-hydroxypropyl)-5-methylpyrimidine
• 英文别名: 2,4-dimethoxy-6-(1-hydroxypropyl)-5-methylpyrimidine；3-(2,6-dimethoxy-5-methylpyrimidin-4-yl)propan-1-ol
• CAS: 156569-43-6
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: BHAIPJZSUFGJHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-6-(3-hydroxypropyl)-5-methylpyrimidine 在 盐酸 、 selenium(IV) oxide 、 三(3,6-二氧杂庚基)胺 、 potassium carbonate 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 5-Hydroxy-6-methyl-1,3,4,5-tetrahydropyrimido[1,6-c][1,3]oxazepine-7,9-dione
  参考文献：
  名称：

  Synthesis of 1-Hydroxy-10-methyl-pyrimido [1, 6-C][1, 3]oxazine and the Oxazepine Derivative, Structural Mimicry of Anti-Constrained Acyclic Thymidine

  摘要：

  A number of pyrimido[1,6-c][1,3]oxazine and -oxazepine derivatives, mimicry analogs of anti-constrained acyclic thymidine, have been prepared via treatment of lithiated 5,6-dimethyl-2,4-dimethoxypyrimidine with benzylchloromethyl ether or oxiran to furnish 2,4-dimethoxy-6-(1-benzyloxyethyl)-5-methylpyrimidine (2) and 2,4-dimethoxy-6-(1 -hydroxypropyl)-5-methylpyrimidine (8), respectively. Debenzylation of 2 afforded 2,4-dimethoxy-6-(1-hydroxyethyl)-5-methylpyrimidine (3). Chloromethylation of 3 and 8 with paraformaldehyde and gaseous hydrogen chloride produced reactive chloromethyl ether intermediates which were converted to the cyclized products 9-methyl-(1H, 2H, 4H, 7H)-pyrimido[1,6-c][1,3]-oxazine (5) and -oxazepine (9)-6,8-dione, respectively. By using selenium dioxide, allylic oxidation of 5 and 9 afforded the target compounds, a racemic mixture of (+/-) 1-hydroxy-9-methyl-(1H, 2H, 4H, 7H)-pyrimido[1,6-c][1,3]-oxazine (6) and -oxazepine (10)-6, 8-dione, respectively. Compounds 5, 6, 7, 9, and 10 were evaluated for activity against human immunodeficiency virus (HIV), herpes simplex virus type 1 (HSV-1) and human cytomegalovirus (HCMV). All of these compounds were inactive.

  DOI：

  10.1080/07328319608002449
• 作为产物：
  描述：

  环氧乙烷 、 2,4-二甲氧基-5,6-二甲基嘧啶 在 lithium diisopropyl amide 作用下， 生成 2,4-dimethoxy-6-(3-hydroxypropyl)-5-methylpyrimidine
  参考文献：
  名称：

  Synthesis of C-6 Pyrimidine Acyclic Nucleoside Analogs as Potential Antiviral Agents

  摘要：

  A number of pyrimidine acyclic nucleosides in which the acyclic moiety is attached to the C-6 position rather than N-1 of the pyrimidine ring have been prepared. This was accomplished via treatment of lithiated 2,4-methoxy-5,6-dimethylpyrimidine, or, 2,4-dimethoxy-6-methylpyrimidine with 1,3-bis-(benzyloxy)-2-propanone, benzyl chloromethyl ether or oxirane, respectively, to give the corresponding key intermediates 6-[3-benzyloxy-2-[(benzyloxy)methyl]-2-hydroxypropyl]-2,4- dimethoxy-5-methylpyrimidine (2a), 6-[3-benzyloxy-2-[(benzyloxy)methyl]-2-hydroxypropyl]-2,4-dimethoxypyrimidine (2b), 6-(2-benzyloxyethyl)-2,4-dimethoxy-5-methylpyrimidine (3), and 2,4-dimethoxy-6-(3-hydroxypropyl)-5-methylpyrimidine (4a). After acidic hydrolysis, followed by debenzylation with boron trichloride these key intermediates were converted to the target C-6 pyrimidine acyclic derivatives. Compounds 6-8b, 11-13, 15, 16, 20, 22, 26, and 29-32 were evaluated for activity against herpes viruses and human immunodeficiency virus. None of the compounds were active against the viruses nor were they cytotoxic at the highest concentration tested.

  DOI：

  10.1080/15257779408013263