6-Dimethoxymethyl-6-methoxymethyl-5,6-dihydro-pyrido[2,3-d]pyrimidine-2,7-diamine | 141292-61-7

• 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: 6-Dimethoxymethyl-6-methoxymethyl-5,6-dihydro-pyrido[2,3-d]pyrimidine-2,7-diamine
• 英文别名: 6-(dimethoxymethyl)-6-(methoxymethyl)-5H-pyrido[2,3-d]pyrimidine-2,7-diamine
• CAS: 141292-61-7
• 化学式: C₁₂H₁₉N₅O₃
• 分子量: 281.315
• InChiKey: DGWQCMSOFGCMRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  117.87
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  sodium methylate 、 盐酸胍 、 3-甲氧基-2-(甲氧基甲基)丙-2-烯腈 生成 6-Dimethoxymethyl-6-methoxymethyl-5,6-dihydro-pyrido[2,3-d]pyrimidine-2,7-diamine
  参考文献：
  名称：

  Syntheses of antibacterial 2,4-diamino-5-benzylpyrimidines. Ormetoprim and trimethoprim

  摘要：

  A general and mild method for the synthesis of 2,4-diamino-5-benzylpyrimidines was achieved by the Friedel-Crafts reaction between 2-(methoxymethylene)-3-methoxypropanenitrile (10) and an activated aromatic substrate followed by treatment with guanidine. The method is illustrated by a synthesis of ormetoprim (2) in 75% overall yield from 3,4-dimethoxytoluene (12). Efficient syntheses of trimethoprim (1) and 2 were also accomplished via prior base-catalyzed 1,3-prototropic isomerization of cinnamonitriles 19 and 20, respectively, followed by condensation with guanidine. 12 was prepared from 3-bromo-4-methoxytoluene by a Cu(I)-catalyzed displacement of bromine by methoxide and 4,5-dimethoxy-2-methylbenzaldehyde was obtained from 12 in 87% yield by a pyridine-catalyzed Vilsmeier reaction using DMF-POCl3.

  DOI：

  10.1021/jo00039a006