4-hydroxy-5-methyl-3,4-dihydro-1H-pyrimido[1,6-c][1,3]oxazine-6,8-dione | 182759-79-1

• 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: 4-hydroxy-5-methyl-3,4-dihydro-1H-pyrimido[1,6-c][1,3]oxazine-6,8-dione
• CAS: 182759-79-1
• 化学式: C₈H₁₀N₂O₄
• 分子量: 198.178
• InChiKey: VELIBISZOHEGQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-hydroxy-5-methyl-3,4-dihydro-1H-pyrimido[1,6-c][1,3]oxazine-6,8-dione 在 4-二甲氨基吡啶 作用下， 反应 14.0h， 以41%的产率得到(5-methyl-6,8-dioxo-3,4-dihydro-1H-pyrimido[1,6-c][1,3]oxazin-4-yl) acetate
  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：

  2,4-dimethoxy-6-(2-hydroxyethyl)-5-methylpyrimidine 在 盐酸 、 selenium(IV) oxide 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 4-hydroxy-5-methyl-3,4-dihydro-1H-pyrimido[1,6-c][1,3]oxazine-6,8-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

文献信息

• Synthesis of 1-Hydroxy-10-methyl-pyrimido [1, 6-C][1, 3]oxazine and the Oxazepine Derivative, Structural Mimicry of Anti-Constrained Acyclic Thymidine
  作者：Ling-Yih Hsu、Dean S. Wise、John C. Drach、Leroy B. Townsend

  DOI：10.1080/07328319608002449

  日期：1996.9

  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.