5-hydroxy-6-methyl-(1-thietan-3-yl)pyrimidine-2,4(1H,3H)-dione | 1417807-82-9

• 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: 5-hydroxy-6-methyl-(1-thietan-3-yl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-Hydroxy-6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1h,3h)-dione；5-hydroxy-6-methyl-1-(thietan-3-yl)pyrimidine-2,4-dione
• CAS: 1417807-82-9
• 化学式: C₈H₁₀N₂O₃S
• 分子量: 214.245
• InChiKey: SLVVYLKSXCBRSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(氯甲基)环硫乙烷 、 5-羟基-6-甲基嘧啶-2,4(1H,3H)-二酮 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以26%的产率得到5-hydroxy-6-methyl-(1-thietan-3-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of new thietanylpyrimidine and thietanylimidazole derivatives

  摘要：

  New thietanyl-substituted derivatives of pyrimidine-2,4(1H,3H)-dione and imidazole were synthesized. The alkylation of 6-methylpyrimidine-2,4(1H,3H)-diones with 2-chloromethylthiirane in water involved the N-1 atom of the pyrimidine ring and afforded 6-methyl-1-(thietan-3-yl)-pyrimidine-2,4(1H,3H)-diones. Under analogous conditions 6-aminopyrimidine-2,4(1H,3H)-dione gave rise to 6-(thietan-3-ylamino)pyrimidine-2,4(1H,3H)-dione. Unsymmetrically substituted 2-methyl-4(5)-nitro- and 5(4)-bromo-2-methyl-4(5)-nitro-1H-imidazoles reacted with 2-chloromethylthiirane to produce mixtures of isomeric 2-methyl-4(5)-nitro-1-(thietan-3-yl)-1H-imidazoles and 5(4)-bromo-2-methyl-4(5)-nitro-1-(thietan-3-yl)-1H-imidazoles.

  DOI：

  10.1134/s1070428013090200

文献信息

• Synthesis of new thietanylpyrimidine and thietanylimidazole derivatives
  作者：S. A. Meshcheryakova、V. A. Kataev

  DOI：10.1134/s1070428013090200

  日期：2013.9

  New thietanyl-substituted derivatives of pyrimidine-2,4(1H,3H)-dione and imidazole were synthesized. The alkylation of 6-methylpyrimidine-2,4(1H,3H)-diones with 2-chloromethylthiirane in water involved the N-1 atom of the pyrimidine ring and afforded 6-methyl-1-(thietan-3-yl)-pyrimidine-2,4(1H,3H)-diones. Under analogous conditions 6-aminopyrimidine-2,4(1H,3H)-dione gave rise to 6-(thietan-3-ylamino)pyrimidine-2,4(1H,3H)-dione. Unsymmetrically substituted 2-methyl-4(5)-nitro- and 5(4)-bromo-2-methyl-4(5)-nitro-1H-imidazoles reacted with 2-chloromethylthiirane to produce mixtures of isomeric 2-methyl-4(5)-nitro-1-(thietan-3-yl)-1H-imidazoles and 5(4)-bromo-2-methyl-4(5)-nitro-1-(thietan-3-yl)-1H-imidazoles.
• Synthesis of thietanyl-substituted pyrimidine-2,4(1H,3H)-dions
  作者：V. A. Kataev、S. A. Meshcheryakova、V. V. Lazarev、V. V. Kuznetsov

  DOI：10.1134/s1070428013050199

  日期：2013.5

  Reactions of 6-methylpyrimidine-2,4(1H,3H)-dione or 5-hydroxy-6-methyl-pyrimidine-2,4(1H,3H)-dione with 2-chloromethylthiirane afforded the corresponding substituted 1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-diones. The calculations in the framework of approximations PBE/3z, B3LYP/6-31G++(d,p) and MP2/6-31G++(d,p) showed that the alkylation occurred at the atom N-1 of the pyrimidine ring.