2-amino-4-(benzyloxy)-8-methylpteridin-7(8H)-one 5-oxide | 1159107-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-amino-4-(benzyloxy)-8-methylpteridin-7(8H)-one 5-oxide
• 英文别名: 2-Amino-8-methyl-5-oxido-4-phenylmethoxypteridin-5-ium-7-one
• CAS: 1159107-88-6
• 化学式: C₁₄H₁₃N₅O₃
• 分子量: 299.289
• InChiKey: XDMGAMQJQHPJSR-UHFFFAOYSA-N

物化性质

• 熔点：
  228 °C
• 沸点：
  633.2±65.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-4-(benzyloxy)-8-methylpteridin-7(8H)-one 5-oxide 、 富马酸二乙酯 以 甲苯 为溶剂， 反应 1.5h， 以89%的产率得到diethyl (2RS,3RS)-2-[2-amino-4-(benzyloxy)-7,8-dihydro-8-methyl-7-oxopteridin-6-yl]-3-hydroxy-butanedioate
  参考文献：
  名称：

  6-（甲基氨基）-5-亚硝基嘧啶的酰化和8-甲基异黄th呤N（5）-氧化物的1，3-偶极环加成。的合成C（6） ，N（8）二取代Isoxanthopterins

  摘要：

  Abstractmagnified imageAcylation of 2‐amino‐4‐(benzyloxy)‐6‐(methylamino)‐5‐nitrosopyrimidine (5) with acetic anhydride or chloroacetic anhydride in the presence of 4‐(dimethylamino)pyridine (DMAP) led to the C(2)‐acylamino derivatives 6 and 7, respectively. In the absence of a base, acetylation did not lead to a product, while chloroacetylation led to the 6‐chloropteridine 11. Chloroacetylation in the presence of Hünig's base provided the pteridinone N(5)‐oxide 10, suggesting that acylation of 5 is readily reversible, and that the unfavourable equilibrium must be displaced by a follow‐up reaction to trap the acylation product. Acylation of 5 with hexadienoyl chloride, followed by intramolecular Diels–Alder reaction, provided the pteridinone 12. A high yielding 1,3‐dipolar cycloaddition of the acylnitrone 10 to electron‐poor and electron‐rich dipolarophiles, followed by spontaneous N,O‐bond cleavage, gave the C(6)‐substituted pteridinones 19a–19e that were deprotected to the pteridine‐4,7(3H,8H)‐diones 20a–20e. Substitution of the 6‐chloropterin 11 provided the 6‐morpholinopteridine 25. Sonogashira coupling yielded the fluorescent [(pteridin‐6‐yl)ethynyl]‐glucopyranoside 26, 6‐ethynylpteridine 28, and 6,6′‐(ethynediyl)bispteridine 29. The alkyne 28 reacted with Me3SiCl and LiBr in MeCN to produce the bromoalkene 31.

  DOI：

  10.1002/hlca.200900009
• 作为产物：
  描述：

  氯乙酸酐 、 2-amino-6-benzyloxy-4-(N-methylamino)-5-nitrosopyrimidine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以78%的产率得到2-amino-4-(benzyloxy)-8-methylpteridin-7(8H)-one 5-oxide
  参考文献：
  名称：

  6-（甲基氨基）-5-亚硝基嘧啶的酰化和8-甲基异黄th呤N（5）-氧化物的1，3-偶极环加成。的合成C（6） ，N（8）二取代Isoxanthopterins

  摘要：

  Abstractmagnified imageAcylation of 2‐amino‐4‐(benzyloxy)‐6‐(methylamino)‐5‐nitrosopyrimidine (5) with acetic anhydride or chloroacetic anhydride in the presence of 4‐(dimethylamino)pyridine (DMAP) led to the C(2)‐acylamino derivatives 6 and 7, respectively. In the absence of a base, acetylation did not lead to a product, while chloroacetylation led to the 6‐chloropteridine 11. Chloroacetylation in the presence of Hünig's base provided the pteridinone N(5)‐oxide 10, suggesting that acylation of 5 is readily reversible, and that the unfavourable equilibrium must be displaced by a follow‐up reaction to trap the acylation product. Acylation of 5 with hexadienoyl chloride, followed by intramolecular Diels–Alder reaction, provided the pteridinone 12. A high yielding 1,3‐dipolar cycloaddition of the acylnitrone 10 to electron‐poor and electron‐rich dipolarophiles, followed by spontaneous N,O‐bond cleavage, gave the C(6)‐substituted pteridinones 19a–19e that were deprotected to the pteridine‐4,7(3H,8H)‐diones 20a–20e. Substitution of the 6‐chloropterin 11 provided the 6‐morpholinopteridine 25. Sonogashira coupling yielded the fluorescent [(pteridin‐6‐yl)ethynyl]‐glucopyranoside 26, 6‐ethynylpteridine 28, and 6,6′‐(ethynediyl)bispteridine 29. The alkyne 28 reacted with Me3SiCl and LiBr in MeCN to produce the bromoalkene 31.

  DOI：

  10.1002/hlca.200900009