6-(4-(Benzyloxy)benzoyl)-5-(4-(benzyloxy)phenyl)-1,3-bis((benzyloxy)methyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine | 145745-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4-(Benzyloxy)benzoyl)-5-(4-(benzyloxy)phenyl)-1,3-bis((benzyloxy)methyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine
• 英文别名: 6-(4-phenylmethoxybenzoyl)-1,3-bis(phenylmethoxymethyl)-5-(4-phenylmethoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-dione
• CAS: 145745-02-4
• 化学式: C₄₉H₄₁N₃O₇
• 分子量: 783.88
• InChiKey: MPHMRJSIVQSERZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(4-(Benzyloxy)benzoyl)-5-(4-(benzyloxy)phenyl)-1,3-bis((benzyloxy)methyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine 在 三甲基氯硅烷 、 水 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 Rigidin
  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：

  1,3-Bis((benzyloxy)methyl)-7-(2,4-dimethoxybenzyl)-2,4-dioxo-5-((trifluoromethanesulfonyl)oxy)pyrrolo<2,3-d>pyrimidine 在 tris-(dibenzylideneacetone)dipalladium(0) 三(2-呋喃基)膦 、 三氟乙酸 、 三氟乙酸酐 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 96.17h， 生成 6-(4-(Benzyloxy)benzoyl)-5-(4-(benzyloxy)phenyl)-1,3-bis((benzyloxy)methyl)-2,4-dioxopyrrolo<2,3-d>pyrimidine
  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.