N-(4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2,2-trifluoroacetamide | 876290-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: N-(4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2,2-trifluoroacetamide
• CAS: 876290-74-3
• 化学式: C₈H₃Cl₂F₃N₄O
• 分子量: 299.039
• InChiKey: QAZXLAVHTORUIV-UHFFFAOYSA-N

物化性质

• 密度：
  1.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.67
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2,2-trifluoroacetamide 在 氢氧化钾 、 三(3,6-二氧杂庚基)胺 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 25.0h， 生成 4,5-dichloro-7-{5'-O-[(1,1-dimethylethyl)dimethylsilyl]-2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidin-2-amine
  参考文献：
  名称：

  7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine:  Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-d-ribofuranose

  摘要：

  The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha-D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution.

  DOI：

  10.1021/jo0516640
• 作为产物：
  描述：

  2-氨基-4-氯吡咯并[2,3-d]嘧啶 在 吡啶 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.58h， 生成 N-(4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine:  Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-d-ribofuranose

  摘要：

  The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha-D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution.

  DOI：

  10.1021/jo0516640