1,3,7-Tribenzyl-5-hydroxy-1,7-dihydro-pyrrolo[2,3-d]pyrimidine-2,4-dione | 145745-03-5

• 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: 1,3,7-Tribenzyl-5-hydroxy-1,7-dihydro-pyrrolo[2,3-d]pyrimidine-2,4-dione
• 英文别名: 1,3,7-Tribenzyl-5-hydroxypyrrolo[2,3-d]pyrimidine-2,4-dione
• CAS: 145745-03-5
• 化学式: C₂₇H₂₃N₃O₃
• 分子量: 437.498
• InChiKey: AEYCWSVRSUKWIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,7-Tribenzyl-5-hydroxy-1,7-dihydro-pyrrolo[2,3-d]pyrimidine-2,4-dione 在 四(三苯基膦)钯 2,4,6-三甲基吡啶 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 1,3,7-Tribenzyl-6-(4-benzyloxy-benzoyl)-5-(4-benzyloxy-phenyl)-1,7-dihydro-pyrrolo[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of a novel pyrrolo[2,3-d]pyrimidine alkaloid, rigidin

  摘要：

  An efficient nine-step synthesis of the brain phosphodiesterase inhibitor, rigidin, has been accomplished in 26% overall yield starting from 6-chlorouracil and ethyl (2,4-dimethoxybenzyl)glycinate. A key feature of the synthetic route reveals a new method for the annulation of pyrrole rings onto pyrimidine rings starting from 6-chlorouracils and N-benzylglycine sodium salts. Thus, initial condensation adducts 7a,b were converted into 5-acetoxypyrroles 8a,b upon warming in acetic anhydride. The readily derived 5-(trifluoromethanesulfonyl)oxy materials 8c,f undergo palladium-catalyzed cross couplings with aryltin reagent 9 and afford C-5 aryl compounds 10a,b. Acylation at the C-6 position in 10a,b was best effected using a mixed anhydride reagent derived from acid 11 and TFAA. The optimal route to ridigin (1d) involved a one-pot deprotection procedure of intermediate lb using excess TMSI followed by heating in water.

  DOI：

  10.1021/jo00054a024
• 作为产物：
  描述：

  6-Chloro-1,3-dibenzyluracil 在 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 1,3,7-Tribenzyl-5-hydroxy-1,7-dihydro-pyrrolo[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of a novel pyrrolo[2,3-d]pyrimidine alkaloid, rigidin

  摘要：

  An efficient nine-step synthesis of the brain phosphodiesterase inhibitor, rigidin, has been accomplished in 26% overall yield starting from 6-chlorouracil and ethyl (2,4-dimethoxybenzyl)glycinate. A key feature of the synthetic route reveals a new method for the annulation of pyrrole rings onto pyrimidine rings starting from 6-chlorouracils and N-benzylglycine sodium salts. Thus, initial condensation adducts 7a,b were converted into 5-acetoxypyrroles 8a,b upon warming in acetic anhydride. The readily derived 5-(trifluoromethanesulfonyl)oxy materials 8c,f undergo palladium-catalyzed cross couplings with aryltin reagent 9 and afford C-5 aryl compounds 10a,b. Acylation at the C-6 position in 10a,b was best effected using a mixed anhydride reagent derived from acid 11 and TFAA. The optimal route to ridigin (1d) involved a one-pot deprotection procedure of intermediate lb using excess TMSI followed by heating in water.

  DOI：

  10.1021/jo00054a024

文献信息

• Synthesis of a novel pyrrolo[2,3-d]pyrimidine alkaloid, rigidin
  作者：Eric D. Edstrom、Yuan Wei

  DOI：10.1021/jo00054a024

  日期：1993.1

  An efficient nine-step synthesis of the brain phosphodiesterase inhibitor, rigidin, has been accomplished in 26% overall yield starting from 6-chlorouracil and ethyl (2,4-dimethoxybenzyl)glycinate. A key feature of the synthetic route reveals a new method for the annulation of pyrrole rings onto pyrimidine rings starting from 6-chlorouracils and N-benzylglycine sodium salts. Thus, initial condensation adducts 7a,b were converted into 5-acetoxypyrroles 8a,b upon warming in acetic anhydride. The readily derived 5-(trifluoromethanesulfonyl)oxy materials 8c,f undergo palladium-catalyzed cross couplings with aryltin reagent 9 and afford C-5 aryl compounds 10a,b. Acylation at the C-6 position in 10a,b was best effected using a mixed anhydride reagent derived from acid 11 and TFAA. The optimal route to ridigin (1d) involved a one-pot deprotection procedure of intermediate lb using excess TMSI followed by heating in water.