5-amino-6-[4,5-dihydro-5-thioxo-1,3,4-oxadiazol-3-yl]-4-methyl-2-phenylthieno[2,3-d]pyrimidine | 569669-29-0

• 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: 5-amino-6-[4,5-dihydro-5-thioxo-1,3,4-oxadiazol-3-yl]-4-methyl-2-phenylthieno[2,3-d]pyrimidine
• CAS: 569669-29-0
• 化学式: C₁₅H₁₁N₅OS₂
• 分子量: 341.417
• InChiKey: CAOYHDLLGUCMNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  93.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  氯乙酸乙酯 、 5-amino-6-[4,5-dihydro-5-thioxo-1,3,4-oxadiazol-3-yl]-4-methyl-2-phenylthieno[2,3-d]pyrimidine 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以60%的产率得到5-amino-6-[2-ethoxycarbonylmethylmercaptooxadiazol-5-yl]-4-methyl-2-phenylthieno-[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and Reactions of Some New Thienopyrimidines

  摘要：

  4-Methyl-6-mercapto-2-phenylpyrimidine-5-carbonitrile (1) was reacted with, different halo compounds, namely ethylchloroacetate, chloroacetone, bromoacetanilide, p-chlorobromoacetanilide, and p-methoxy chloroacetanilide in ethanol in the presence of sodium acetate yielded the corresponding S-alkylated derivatives (2a-e). The latter compounds underwent cyclization into thienopyrimidines (4a-e) upon treatment with sodium ethoxide in ethanol. The reaction of (4a) with hydrazine hydrate led to the formation. of 5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidine-2-carbohydrazide (5). Compound (5) was reacted with a variety of reagents to produce other new thienopyrimidines as well as oxadiazolylthienopyrimidines (6, 11).

  DOI：

  10.1080/10426500307807
• 作为产物：
  描述：

  3-Amino-4-methyl-6-phenyl-thieno<2,3-d>pyrimidin-2-carbonsaeureethylester 在 吡啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-amino-6-[4,5-dihydro-5-thioxo-1,3,4-oxadiazol-3-yl]-4-methyl-2-phenylthieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and Reactions of Some New Thienopyrimidines

  摘要：

  4-Methyl-6-mercapto-2-phenylpyrimidine-5-carbonitrile (1) was reacted with, different halo compounds, namely ethylchloroacetate, chloroacetone, bromoacetanilide, p-chlorobromoacetanilide, and p-methoxy chloroacetanilide in ethanol in the presence of sodium acetate yielded the corresponding S-alkylated derivatives (2a-e). The latter compounds underwent cyclization into thienopyrimidines (4a-e) upon treatment with sodium ethoxide in ethanol. The reaction of (4a) with hydrazine hydrate led to the formation. of 5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidine-2-carbohydrazide (5). Compound (5) was reacted with a variety of reagents to produce other new thienopyrimidines as well as oxadiazolylthienopyrimidines (6, 11).

  DOI：

  10.1080/10426500307807