2-Amino-6--4-chloropyrimidine | 155670-18-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Amino-6--4-chloropyrimidine
• 英文别名: 2-[(2-Amino-6-chloropyrimidin-4-yl)-benzylamino]acetic acid
• CAS: 155670-18-1
• 化学式: C₁₃H₁₃ClN₄O₂
• 分子量: 292.725
• InChiKey: JOJAVJOWEIAEQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Amino-6--4-chloropyrimidine 在 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.7h， 生成 5-Amino-1-benzyl-7-methoxy-2-(trifluoroacetyl)imidazo<1,2-c>pyrimidin-3-one
  参考文献：
  名称：

  Cyclodehydration of 5-[(Carboxymethyl)amino]pyrimidines. Synthesis and Characterization of Novel Mesoionic Imidazo[1,2-c]pyrimidin-3-ones

  摘要：

  The cyclodehydration of 5-(carboxymethyl)amino-substituted pyrimidines using acid anhydrides has provided a general synthesis of novel mesoionic imidazo [1,2-c] pyrimidin-3-one compounds. The complete structural characterization and chemical reactivity studies of these compounds, including X-ray crystal structures for compounds 9c and 16a, were determined. Compounds lacking a blocking group at N-1 were found to undergo clean alkylation at this position, under basic reaction conditions, with substituted alkyl chlorides. Imidazo[1,2-c] pyrimidin-3-ones having a benzyl group at N-1 were found to undergo substitution reactions on the pyrimidine ring in the presence of basic nucleophiles. Thus, replacement of a 5-methylthio over a 7-chloro substituent was favored, whereas the 7-chloro group was substituted in compounds where a 6-amino substituent was present. Exposure of imidazo[1,2-c]pyrimidin-3-ones to aqueous acid results in the ring opening of the five-membered ring with subsequent loss of carbon dioxide or trifluoroacetate in an overall net reversion of the cyclodehydration reaction. Examination of the X-ray structures obtained for compounds 9c and 16a indicated that the five-membered ring was not aromatic, but rather a combination of a ring-opened valence tautomer and a charge-delocalized resonance hybrid structure.

  DOI：

  10.1021/jo00088a031
• 作为产物：
  描述：

  2-氨基-4,6-二氯嘧啶 、 N-benzylglycine sodium salt 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85.5%的产率得到2-Amino-6--4-chloropyrimidine
  参考文献：
  名称：

  Cyclodehydration of 5-[(Carboxymethyl)amino]pyrimidines. Synthesis and Characterization of Novel Mesoionic Imidazo[1,2-c]pyrimidin-3-ones

  摘要：

  The cyclodehydration of 5-(carboxymethyl)amino-substituted pyrimidines using acid anhydrides has provided a general synthesis of novel mesoionic imidazo [1,2-c] pyrimidin-3-one compounds. The complete structural characterization and chemical reactivity studies of these compounds, including X-ray crystal structures for compounds 9c and 16a, were determined. Compounds lacking a blocking group at N-1 were found to undergo clean alkylation at this position, under basic reaction conditions, with substituted alkyl chlorides. Imidazo[1,2-c] pyrimidin-3-ones having a benzyl group at N-1 were found to undergo substitution reactions on the pyrimidine ring in the presence of basic nucleophiles. Thus, replacement of a 5-methylthio over a 7-chloro substituent was favored, whereas the 7-chloro group was substituted in compounds where a 6-amino substituent was present. Exposure of imidazo[1,2-c]pyrimidin-3-ones to aqueous acid results in the ring opening of the five-membered ring with subsequent loss of carbon dioxide or trifluoroacetate in an overall net reversion of the cyclodehydration reaction. Examination of the X-ray structures obtained for compounds 9c and 16a indicated that the five-membered ring was not aromatic, but rather a combination of a ring-opened valence tautomer and a charge-delocalized resonance hybrid structure.

  DOI：

  10.1021/jo00088a031

文献信息

• Cyclodehydration of 5-[(Carboxymethyl)amino]pyrimidines. Synthesis and Characterization of Novel Mesoionic Imidazo[1,2-c]pyrimidin-3-ones
  作者：Eric D. Edstrom、Yuan Wei、Michelle Gordon

  DOI：10.1021/jo00088a031

  日期：1994.5

  The cyclodehydration of 5-(carboxymethyl)amino-substituted pyrimidines using acid anhydrides has provided a general synthesis of novel mesoionic imidazo [1,2-c] pyrimidin-3-one compounds. The complete structural characterization and chemical reactivity studies of these compounds, including X-ray crystal structures for compounds 9c and 16a, were determined. Compounds lacking a blocking group at N-1 were found to undergo clean alkylation at this position, under basic reaction conditions, with substituted alkyl chlorides. Imidazo[1,2-c] pyrimidin-3-ones having a benzyl group at N-1 were found to undergo substitution reactions on the pyrimidine ring in the presence of basic nucleophiles. Thus, replacement of a 5-methylthio over a 7-chloro substituent was favored, whereas the 7-chloro group was substituted in compounds where a 6-amino substituent was present. Exposure of imidazo[1,2-c]pyrimidin-3-ones to aqueous acid results in the ring opening of the five-membered ring with subsequent loss of carbon dioxide or trifluoroacetate in an overall net reversion of the cyclodehydration reaction. Examination of the X-ray structures obtained for compounds 9c and 16a indicated that the five-membered ring was not aromatic, but rather a combination of a ring-opened valence tautomer and a charge-delocalized resonance hybrid structure.