2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone sulfuric acid salt | 142811-38-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone sulfuric acid salt
• 英文别名: 2-amino-4-chloro-5-nitro-1H-pyrimidin-6-one;sulfuric acid
• CAS: 142811-38-9
• 化学式: C₄H₃ClN₄O₃*H₂O₄S
• 分子量: 288.625
• InChiKey: DBDCXKNOUMFXDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.74
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  196
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone sulfuric acid salt 、 1-amino-2(S)-(benzylamino)pentane 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以93%的产率得到2-amino-6-<<(2'(S)-benzylamino)pentyl>amino>-5-nitro-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

• 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.