2-amino-4-bromo-5,6-dihydro-5-methylpyrido<2,3-d>pyrimidin-7(8H)-one | 100475-76-1

• 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-bromo-5,6-dihydro-5-methylpyrido<2,3-d>pyrimidin-7(8H)-one
• 英文别名: 2-amino-4-bromo-5-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one；2-amino-4-bromo-5-methyl-6,8-dihydro-5H-pyrido[2,3-d]pyrimidin-7-one
• CAS: 100475-76-1
• 化学式: C₈H₉BrN₄O
• 分子量: 257.09
• InChiKey: BUODBUKRRXHQOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-bromo-5,6-dihydro-5-methylpyrido<2,3-d>pyrimidin-7(8H)-one 在 一水合肼 作用下， 反应 0.5h， 以90%的产率得到2-Amino-4-hydrazino-5-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Victory, Pedro; Crespo, Ana; Garriga, Miquel, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 245 - 247

  摘要：

  DOI：
• 作为产物：
  描述：

  6-cyanamino-5-cyano-3,4-dihydro-4-methyl-2-pyridone 在 氢溴酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-amino-4-bromo-5,6-dihydro-5-methylpyrido<2,3-d>pyrimidin-7(8H)-one
  参考文献：
  名称：

  Victory, Pedro; Garriga, Miquel, Heterocycles, 1985, vol. 23, # 8, p. 1947 - 1950

  摘要：

  DOI：

文献信息

• An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones
  作者：José I. Borrell、Jordi Teixidó、Blanca Martínez-Teipel、Blanca Serra、Josep Lluís Matallana、Marta Costa、Xavier Batllori

  DOI：10.1135/cccc19960901

  日期：——

  An unequivocal set of procedures for the synthesis of 4-amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones (7) and 2-amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones (8), in a maximum of four steps from an α,β-unsaturated ester 1, is reported. Thus, the acid hydrolysis of the 2,4-diaminopyrido[2,3-d]pyrimidines 3 yields the 4-amino-2-oxopyrido[2,3-d]pyrimidines 7 while the cyclization of the Michael adducts 9 (formed by reaction of 1 and methyl cyanoacetate) with guanidine affords the corresponding 2-amino-4-oxopyrido[2,3-d]pyrimidines 8. Both isomers were also obtained by hydrolysis of the 4-amino-2-bromo- and 2-amino-4-bromo-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones 5 and 6, respectively.

  一种无歧义的程序集，用于从α，β-不饱和酯1最多经过四个步骤合成4-氨基-1,5,6,8-四氢吡啶并[2,3-d]嘧啶-2,7-二酮（7）和2-氨基-3,5,6,8-四氢吡啶并[2,3-d]嘧啶-4,7-二酮（8）。因此，2,4-二氨基吡啶并[2,3-d]嘧啶3的酸水解产生4-氨基-2-氧代吡啶并[2,3-d]嘧啶7，而Michael加合物9（由1和氰乙酸甲酯反应形成）与胍嘧啶的环化则得到相应的2-氨基-4-氧代吡啶并[2,3-d]嘧啶8。这两种异构体也可通过4-氨基-2-溴和2-氨基-4-溴-5,6-二氢吡啶并[2,3-d]嘧啶-7(8H)-酮5和6的水解分别获得。
• Teixido, Jordi; Borrell, Jose I.; Serra, Blanca, Heterocycles, 1999, vol. 50, # 2, p. 739 - 756
  作者：Teixido, Jordi、Borrell, Jose I.、Serra, Blanca、Matallana, Josep Lluis、Colominas, Carles、Carrion, Francisco、Pascual, Rosalia、Falco, Josep Lluis、Batllori, Xavier

  DOI：——

  日期：——
• Cyclization of 5-Cyano-6-cyanoimino-3,4-dihydropyridin-2(1H)-ones with Amines
  作者：José I. Borrell、Núria Mont、Francisco Carrión、Jordi Teixidó

  DOI：10.3987/com-09-11860

  日期：——

  The cyclization of 5-cyano-6-cyanoimino-3,4-dihydropyridin-2(1h)-ones with amines, leading to pyrido[2,3-d]pyrimidines, is studied. Four play all important role oil the direction of cyclization: (1) the planarity of the reaction area; (2) the cyclization proceeds by the nucleophilic attack of all amidine onto ail electrophilic group which call be either a cyano group or all alkylamidine; (3) the basicity of the amine plays all important role, the ionization Of the Substrate making more difficult the formation of the aforementioned amidine which is needed for the cyclization; and (4) the nucleophilic attack and the tautomerization of the cyclization product are processes which call occur practically Simultaneously, so that the electronic movement involved in the tautomerization process coincides with the one which happens In the nucleophilic attack, both processes promoting each other.
• VICTORY, P.;GARRIGA, M., HETEROCYCLES, 1985, 23, N 8, 1947-1950
  作者：VICTORY, P.、GARRIGA, M.

  DOI：——

  日期：——
• VICTORY, PEDRO;CRESPO, ANA;GARRIGA, MIQUEL;NOMEN, ROSA, J. HETEROCYCL. CHEM., 25,(1988) N 1, 245-247
  作者：VICTORY, PEDRO、CRESPO, ANA、GARRIGA, MIQUEL、NOMEN, ROSA

  DOI：——

  日期：——