ethyl N-(6-ethoxycarbonyl-2-methylthiothieno<2,3-d>pyrimidin-5-yl)formimidate | 113918-00-6

• 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: ethyl N-(6-ethoxycarbonyl-2-methylthiothieno<2,3-d>pyrimidin-5-yl)formimidate
• 英文别名: ethyl 2-methylthio-5-ethoxymethyleneaminothieno<2,3-d>pyrimidine-6-carboxylate；Ethyl 5-(ethoxymethylideneamino)-2-methylsulfanylthieno[2,3-d]pyrimidine-6-carboxylate
• CAS: 113918-00-6
• 化学式: C₁₃H₁₅N₃O₃S₂
• 分子量: 325.412
• InChiKey: VXVCPMXRHNVEQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl N-(6-ethoxycarbonyl-2-methylthiothieno<2,3-d>pyrimidin-5-yl)formimidate 在 甲基肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到ethyl 5-amino-2-methylthiothieno<2,3-d>pyrimidine-6-carboxylate
  参考文献：
  名称：

  Reaction of ethyl N-(6-ethoxycarbonyl-2-methylthiothieno[2,3-d]-pyrimidin-5-yl) formimidate with alkyl- and arylhydrazines: Formation of modified thieno[2,3-d]pyrimidines and thieno[2,3-d:4,5-d]dipyrimidin-4-ones

  摘要：

  The reaction of ethyl N-(6-ethoxycarbonyl-2-methylthiothieno[2,3-d]pyrimidin-5-yl)formimidate (1) with methylhydrazine, N,N'-dimethyl- and N,N'-diphenylhydrazines separately in refluxing ethanol resulted in hydrolysis of formimidate group to give ethyl 5-amino-2-methylthiothieno[2,3-d] pyrimidine-6-carboxylate (2). The reaction on 1 with methylhydrazine without solvent afforded ethyl 5-amino-2-(1-methylhydrazino)thieno[2,3-d]pyrimidine-6-carboxylate (3), which underwent hydrazone formation with p-nitrobenzaldehyde to give 4. Treatment of 1 with NN-dimethylhydrazine afforded a mixture of 3-dimethylamino-7-methylthiothieno[2,3-d:4,5-d']dipyrimidin-4(3H)-one (5) and 2. Displacement of methylthio group in 5 with morpholine, piperidine and 4-methylpiperazine gave the corresponding 7-substituted derivatives 6a-c. The reaction of 1 with para-substituted phenylhydrazines resulted in the formation of 3-(p-substituted phenylamino)-7-methylthiothieno[2,3-d:4,5-d']dipyrimidin-4 (3H)-ones (7a-c).

  DOI：

  10.1002/prac.19943360211
• 作为产物：
  描述：

  ethyl 5-amino-2-methylthiothieno<2,3-d>pyrimidine-6-carboxylate 、 原甲酸三乙酯 在 乙酸酐 作用下， 反应 4.0h， 以93%的产率得到ethyl N-(6-ethoxycarbonyl-2-methylthiothieno<2,3-d>pyrimidin-5-yl)formimidate
  参考文献：
  名称：

  2-甲基硫代噻吩并-[2,3-d]嘧啶-6-羧酸乙酯的5-氨基衍生物的合成及其与肼的反应

  摘要：

  DOI：

  10.1007/bf00473473

文献信息

• Reaction of ethyl N-(6-ethoxycarbonyl-2-methylthiothieno[2,3-d]-pyrimidin-5-yl) formimidate with alkyl- and arylhydrazines: Formation of modified thieno[2,3-d]pyrimidines and thieno[2,3-d:4,5-d]dipyrimidin-4-ones
  作者：S. Tumkevicius

  DOI：10.1002/prac.19943360211

  日期：——

  The reaction of ethyl N-(6-ethoxycarbonyl-2-methylthiothieno[2,3-d]pyrimidin-5-yl)formimidate (1) with methylhydrazine, N,N'-dimethyl- and N,N'-diphenylhydrazines separately in refluxing ethanol resulted in hydrolysis of formimidate group to give ethyl 5-amino-2-methylthiothieno[2,3-d] pyrimidine-6-carboxylate (2). The reaction on 1 with methylhydrazine without solvent afforded ethyl 5-amino-2-(1-methylhydrazino)thieno[2,3-d]pyrimidine-6-carboxylate (3), which underwent hydrazone formation with p-nitrobenzaldehyde to give 4. Treatment of 1 with NN-dimethylhydrazine afforded a mixture of 3-dimethylamino-7-methylthiothieno[2,3-d:4,5-d']dipyrimidin-4(3H)-one (5) and 2. Displacement of methylthio group in 5 with morpholine, piperidine and 4-methylpiperazine gave the corresponding 7-substituted derivatives 6a-c. The reaction of 1 with para-substituted phenylhydrazines resulted in the formation of 3-(p-substituted phenylamino)-7-methylthiothieno[2,3-d:4,5-d']dipyrimidin-4 (3H)-ones (7a-c).
• Synthesis of 5-amino derivatives of ethyl 2-methylthiothieno-[2,3-d]pyrimidine-6-carboxylate and their reaction with hydrazine
  作者：S. P. Tumkyavichyus、R. I. Matulyauskene

  DOI：10.1007/bf00473473

  日期：1987.8