(4-Amino-5,6-dimethyl-thieno<2,3-d>pyrimid-2-yl-thio)-essigsaeure | 177355-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: (4-Amino-5,6-dimethyl-thieno<2,3-d>pyrimid-2-yl-thio)-essigsaeure
• 英文别名: Acetic acid, 2-[(4-amino-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)thio]-；2-(4-amino-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)sulfanylacetic acid
• CAS: 177355-93-0
• 化学式: C₁₀H₁₁N₃O₂S₂
• 分子量: 269.348
• InChiKey: PSMZZJQQSGKUCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  potassium thioacyanate 、 2-氯-N-(3-氰基-4,5-二甲基-2-噻吩基)乙酰胺 在 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以59%的产率得到(4-Amino-5,6-dimethyl-thieno<2,3-d>pyrimid-2-yl-thio)-essigsaeure
  参考文献：
  名称：

  Neue Synthese von substituierten 4-Amino-chinazolinen und deren Heteroanalogen

  摘要：

  N-Chloracetyl-anthranilonitriles react with potassium thiocyanate in the presence of alcohol to the (4-amino-quinazolin-2-yl-thio)-acetic acid ester (5). In the presence of water or primary amine the acetic acid derivative (6) or the acetic acid amide derivatives (7) are obtained. 2,4-Diamino-quinazolines (8) arise if vigorous reaction conditions are employed. With 2-chloracetylamino-cyclopent-1-en-carbonitrile as starting material the pyrimidines (11) are formed from the reaction with potassium thiocyanate. Analogously, (4-pyrimidyl-2-yl-seleno)-acetic acid ester (12) and (thiazolo[4,5d]pyrimid-2-yl-seleno)-acetic acid derivatives (16)can be prepared with potassium selenocyanate. N-Chloracetyl derivatives of 5-membered heterocycles with enamino-nitrile structure (13, 15, 18, 20) react with potassium thiocyanate to yield thieno[2,3-d]-, thiazolo[4,5-d]-, pyrrolo[2,3-d]-, furo[2,3-d]and pyrazolo[4,3-d]pyrimidines (14, 16, 19a, 19b, 21).

  DOI：

  10.1002/prac.19963380144

文献信息

• Neue Synthese von substituierten 4-Amino-chinazolinen und deren Heteroanalogen
  作者：K. Gewald、H. Sch�fer、K. Eckert、T. Jeschke

  DOI：10.1002/prac.19963380144

  日期：——

  N-Chloracetyl-anthranilonitriles react with potassium thiocyanate in the presence of alcohol to the (4-amino-quinazolin-2-yl-thio)-acetic acid ester (5). In the presence of water or primary amine the acetic acid derivative (6) or the acetic acid amide derivatives (7) are obtained. 2,4-Diamino-quinazolines (8) arise if vigorous reaction conditions are employed. With 2-chloracetylamino-cyclopent-1-en-carbonitrile as starting material the pyrimidines (11) are formed from the reaction with potassium thiocyanate. Analogously, (4-pyrimidyl-2-yl-seleno)-acetic acid ester (12) and (thiazolo[4,5d]pyrimid-2-yl-seleno)-acetic acid derivatives (16)can be prepared with potassium selenocyanate. N-Chloracetyl derivatives of 5-membered heterocycles with enamino-nitrile structure (13, 15, 18, 20) react with potassium thiocyanate to yield thieno[2,3-d]-, thiazolo[4,5-d]-, pyrrolo[2,3-d]-, furo[2,3-d]and pyrazolo[4,3-d]pyrimidines (14, 16, 19a, 19b, 21).