6-<(2(S)-aminopentyl)amino>-2,5-diamino-4(3H)-pyrimidinone | 142841-47-2

• 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: 6-<(2(S)-aminopentyl)amino>-2,5-diamino-4(3H)-pyrimidinone
• 英文别名: 2,5-diamino-4-[[(2S)-2-aminopentyl]amino]-1H-pyrimidin-6-one
• CAS: 142841-47-2
• 化学式: C₉H₁₈N₆O
• 分子量: 226.282
• InChiKey: FEYBSUJNNRAMQK-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  132
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-<(2(S)-aminopentyl)amino>-2,5-diamino-4(3H)-pyrimidinone 生成 6-propyl-7,8-dihydropterin 、 2-Amino-6-((S)-2-amino-pentylamino)-5-hydroxy-3H-pyrimidin-4-one 、 6(S)-propyl-5,6,7,8-tetrahydropterin
  参考文献：
  名称：

  Synthesis of tetrahydropteridine C6-stereoisomers, including N5-formyl-(6S)-tetrahydrofolic acid

  摘要：

  Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone, the nitro group reduced, and the amine deprotected. oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer. Thus, 6(R)- and 6(S)-propyltetrahydropterin were stereospecifically synthesized (99% enantiomeric purity) in good yield from D- and L-norvaline, respectively. Reductive alkylation of (p-aminobenzoyl)-L-glutamate with a nitropyrimidine aldehyde derived from D- or L-serine similarly afforded, after cyclization and reduction, (6R)- or (6S)-tetrahydrofolic acid. The latter was then converted to the natural isomer of leucovorin by regioselective N5-formylation with carbonyl diimidazole/formic acid without loss of enantiomeric purity.

  DOI：

  10.1021/jo00042a030
• 作为产物：
  描述：

  N-benzylidene-L-norvalinamide 在 palladium on barium sulfate dimethyl sulfide borane 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 28.0h， 生成 6-<(2(S)-aminopentyl)amino>-2,5-diamino-4(3H)-pyrimidinone
  参考文献：
  名称：

  Synthesis of tetrahydropteridine C6-stereoisomers, including N5-formyl-(6S)-tetrahydrofolic acid

  摘要：

  Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone, the nitro group reduced, and the amine deprotected. oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer. Thus, 6(R)- and 6(S)-propyltetrahydropterin were stereospecifically synthesized (99% enantiomeric purity) in good yield from D- and L-norvaline, respectively. Reductive alkylation of (p-aminobenzoyl)-L-glutamate with a nitropyrimidine aldehyde derived from D- or L-serine similarly afforded, after cyclization and reduction, (6R)- or (6S)-tetrahydrofolic acid. The latter was then converted to the natural isomer of leucovorin by regioselective N5-formylation with carbonyl diimidazole/formic acid without loss of enantiomeric purity.

  DOI：

  10.1021/jo00042a030

文献信息

• US5198547A
  申请人：——

  公开号：US5198547A

  公开（公告）日：1993-03-30
• US5350851A
  申请人：——

  公开号：US5350851A

  公开（公告）日：1994-09-27
• Synthesis of tetrahydropteridine C6-stereoisomers, including N5-formyl-(6S)-tetrahydrofolic acid
  作者：Steven W. Bailey、Rama Y. Chandrasekaran、June E. Ayling

  DOI：10.1021/jo00042a030

  日期：1992.7

  Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone, the nitro group reduced, and the amine deprotected. oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer. Thus, 6(R)- and 6(S)-propyltetrahydropterin were stereospecifically synthesized (99% enantiomeric purity) in good yield from D- and L-norvaline, respectively. Reductive alkylation of (p-aminobenzoyl)-L-glutamate with a nitropyrimidine aldehyde derived from D- or L-serine similarly afforded, after cyclization and reduction, (6R)- or (6S)-tetrahydrofolic acid. The latter was then converted to the natural isomer of leucovorin by regioselective N5-formylation with carbonyl diimidazole/formic acid without loss of enantiomeric purity.