ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)pyrimidine-5-carboxylate | 671188-44-6

• 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 2-amino-4-(2-ethoxy-2-oxoethyl)pyrimidine-5-carboxylate
• 英文别名: ethyl 2-amino-4-(2-ethoxycarbonylmethyl)pyrimidine-5-carboxylate
• CAS: 671188-44-6
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: LKGFFKNGQXBIGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)pyrimidine-5-carboxylate 、 N,N-二甲基甲酰胺二甲基缩醛 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到ethyl 2-[(dimethylamino)methyleneamino]-4-(2-ethoxy-2-oxoethyl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  Transformations of Diethyl 2-[(Dimethylamino)methylene]-3-oxopentanedioate. A Simple Synthesis of Substituted 2-Amino-5-oxo-5,6-dihydropyrido[4,3-d]pyrimidine-8-carboxylates

  摘要：

  Diethyl 2-[(dimethylamino)methylene]-3-oxopentanedioate (2), prepared from acetone-1,3-dicarboxylates (1) and N,N-dimethylformamide dimethyl acetal (DMFDMA) was, without isolation, transformed by treatment with guanidine hydrochloride into ethyl 2-amino-4-(2-ethoxycarbonylmethyl)-pyrimidine-5-carboxylate (3). Compound 3 was transformed with DMFDMA first into intermediate 4 and with an excess of DMFDMA into ethyl 4-[1-(dimethylamino)-3-ethoxy-3-oxoprop-1-en-2-yl]-2-[(dimethylamino)methyle neamino]pyrimidine-5-carboxylate (5). By treatment of compound 5 with ammonia, primary amines, hydrazine or hydroxylamine intermediates 6a-j were formed, which cyclized into 6-substituted 2-amino-5-oxo-5,6-dihydropyrido[4,3-d]pyridine-8-carboxylates (7a-j).

  DOI：

  10.3987/com-08-s(f)90
• 作为产物：
  描述：

  盐酸胍 、 diethyl 2-((dimethylamino)methylene)-3-oxopentanedioate 以 乙醇 为溶剂， 反应 1.0h， 以290 mg的产率得到ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  Transformations of Diethyl 2-[(Dimethylamino)methylene]-3-oxopentanedioate. A Simple Synthesis of Substituted 2-Amino-5-oxo-5,6-dihydropyrido[4,3-d]pyrimidine-8-carboxylates

  摘要：

  Diethyl 2-[(dimethylamino)methylene]-3-oxopentanedioate (2), prepared from acetone-1,3-dicarboxylates (1) and N,N-dimethylformamide dimethyl acetal (DMFDMA) was, without isolation, transformed by treatment with guanidine hydrochloride into ethyl 2-amino-4-(2-ethoxycarbonylmethyl)-pyrimidine-5-carboxylate (3). Compound 3 was transformed with DMFDMA first into intermediate 4 and with an excess of DMFDMA into ethyl 4-[1-(dimethylamino)-3-ethoxy-3-oxoprop-1-en-2-yl]-2-[(dimethylamino)methyle neamino]pyrimidine-5-carboxylate (5). By treatment of compound 5 with ammonia, primary amines, hydrazine or hydroxylamine intermediates 6a-j were formed, which cyclized into 6-substituted 2-amino-5-oxo-5,6-dihydropyrido[4,3-d]pyridine-8-carboxylates (7a-j).

  DOI：

  10.3987/com-08-s(f)90