5-methyl-1-[(1-(pivaloyloxymethyl)-1H-1,2,3-triazol-4-yl)methyl]pyrimidine-2,4(1H,3H)-dione | 1352744-18-3

• 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-methyl-1-[(1-(pivaloyloxymethyl)-1H-1,2,3-triazol-4-yl)methyl]pyrimidine-2,4(1H,3H)-dione
• CAS: 1352744-18-3
• 化学式: C₁₄H₁₉N₅O₄
• 分子量: 321.336
• InChiKey: AFDZTRDKGRMTFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111.87
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-methyl-1-[(1-(pivaloyloxymethyl)-1H-1,2,3-triazol-4-yl)methyl]pyrimidine-2,4(1H,3H)-dione 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以88%的产率得到5-methyl-1-[1H-1,2,3-triazol-4-ylmethyl]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-nucleosides via the post-triazole N-alkylation

  摘要：

  2-Substituted-2H-1,2,3-triazolo-nucleosides with 3-phosphonopropyl, 2-hydroxyethyl, 2-cyanoethyl, carbamoylmethyl, or 1-deoxy-2,5-anhydro-D-mannitol-1-yl on the triazole N-2 nitrogen atom were obtained via the DBU-promoted N-alkylation of 3-(pivaloyloxymethyl)-1-[(NH-1,2,3-triazol-4-yl)methyl] thymine with diethyl 3-bromopropylphoshonate, 2-bromoethanol, acrylonitrile, methyl bromoacetate, or 3,4,6-tris(O-benzoyl)-2,5-anhydro-D-mannitol 1-tosylate. The N-2/N-1 regioselectivity of the alkylation varied from 57/43 (methyl bromoacetate) to 97/3 (diethyl 3-bromopropylphoshonate). The 1-substituted-1H-1,2,3-triazoles, when formed in the appreciated amount in the alkylation reaction, were converted into the corresponding 1-substituted-1H-1,2,3-triazolo-nucleosides. The substitution pattern of 2-substituted-2H-1,2,3-triazolo-nucleosides was confirmed by H-1-N-15 HMBC NMR spectra; the triazole nitrogen atoms were identified through their correlations with the triazole exo-cyclic protons. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.067
• 作为产物：
  描述：

  azidomethyl pivalate 、 N-1-propargylthymine 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到5-methyl-1-[(1-(pivaloyloxymethyl)-1H-1,2,3-triazol-4-yl)methyl]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-nucleosides via the post-triazole N-alkylation

  摘要：

  2-Substituted-2H-1,2,3-triazolo-nucleosides with 3-phosphonopropyl, 2-hydroxyethyl, 2-cyanoethyl, carbamoylmethyl, or 1-deoxy-2,5-anhydro-D-mannitol-1-yl on the triazole N-2 nitrogen atom were obtained via the DBU-promoted N-alkylation of 3-(pivaloyloxymethyl)-1-[(NH-1,2,3-triazol-4-yl)methyl] thymine with diethyl 3-bromopropylphoshonate, 2-bromoethanol, acrylonitrile, methyl bromoacetate, or 3,4,6-tris(O-benzoyl)-2,5-anhydro-D-mannitol 1-tosylate. The N-2/N-1 regioselectivity of the alkylation varied from 57/43 (methyl bromoacetate) to 97/3 (diethyl 3-bromopropylphoshonate). The 1-substituted-1H-1,2,3-triazoles, when formed in the appreciated amount in the alkylation reaction, were converted into the corresponding 1-substituted-1H-1,2,3-triazolo-nucleosides. The substitution pattern of 2-substituted-2H-1,2,3-triazolo-nucleosides was confirmed by H-1-N-15 HMBC NMR spectra; the triazole nitrogen atoms were identified through their correlations with the triazole exo-cyclic protons. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.067