2-Methyl-5-bromo-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidine | 144750-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 2-Methyl-5-bromo-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidine
• 英文别名: 3-Bromo-1,5-dihydro-6-methyl-4H-pyrazolo[3,4-d]pyrimidin-4-one；3-bromo-6-methyl-2,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
• CAS: 144750-84-5
• 化学式: C₆H₅BrN₄O
• 分子量: 229.036
• InChiKey: TVHDWXFEGVXMNE-UHFFFAOYSA-N

物化性质

• 密度：
  2.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methyl-5-bromo-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidine 在 palladium on activated charcoal 、 四(三苯基膦)钯 copper(l) iodide 、 氢气 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 25.0~105.0 ℃ 、344.73 kPa 条件下， 反应 3.0h， 生成 Dimethyl N-<4-<2-(2-methyl-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate
  参考文献：
  名称：

  Synthesis of pyrazolo 3,4-pyrimidine analogues of the potent agent N-4-2-2-amino-4 3-oxo-7-pyrrolo 2,3-pyrimidin-5-yl ethylbenzoyl-L-glutamic acid (LY231514)

  摘要：

  Several pyrazolo[3,4-d]pyrimidine analogues of the potent antitumor agent N-{4-12-(2-amino-4(3H)-oxo-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514, 5) have been prepared. A principal synthetic step proved to be a palladium-catalyzed C-C coupling of the 5-halo-substituted pyrazolo[3,4-d]pyrimidines 12-15 with dimethyl 4-ethynylbenzoyl-L-glutamate (16). An additional pyrazolo[3,4-d]pyrimidine analogue of 5 possessing an isofolic acid bridge unit (-NHCH2-) was prepared by reductive alkylation of diethyl 4-formylbenzoyl-L-glutamate (31) with 2-methyl-5-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidine (30). Only compound 26 proved to have in vitro cell growth inhibitory activity.

  DOI：

  10.1016/s0040-4020(01)80479-8
• 作为产物：
  描述：

  1,5-二氢-6-甲基-4H-吡唑并[3,4-d]嘧啶-4-酮 在 溴 作用下， 以 水 为溶剂， 以81%的产率得到2-Methyl-5-bromo-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidine
  参考文献：
  名称：

  Synthesis of pyrazolo 3,4-pyrimidine analogues of the potent agent N-4-2-2-amino-4 3-oxo-7-pyrrolo 2,3-pyrimidin-5-yl ethylbenzoyl-L-glutamic acid (LY231514)

  摘要：

  Several pyrazolo[3,4-d]pyrimidine analogues of the potent antitumor agent N-{4-12-(2-amino-4(3H)-oxo-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514, 5) have been prepared. A principal synthetic step proved to be a palladium-catalyzed C-C coupling of the 5-halo-substituted pyrazolo[3,4-d]pyrimidines 12-15 with dimethyl 4-ethynylbenzoyl-L-glutamate (16). An additional pyrazolo[3,4-d]pyrimidine analogue of 5 possessing an isofolic acid bridge unit (-NHCH2-) was prepared by reductive alkylation of diethyl 4-formylbenzoyl-L-glutamate (31) with 2-methyl-5-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidine (30). Only compound 26 proved to have in vitro cell growth inhibitory activity.

  DOI：

  10.1016/s0040-4020(01)80479-8

文献信息

• 6-alkyl dihydropyrazolopyrimidinone compounds as PDE2 inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10160762B2

  公开（公告）日：2018-12-25

  The present invention is directed to 6-alkyl dihydropyrazolopyrimidinone compounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypo-function or basal ganglia dysfunction.

  本发明涉及式（I）的6-烷基二氢吡唑嘧啶酮化合物，该化合物可作为治疗剂用于治疗与磷酸二酯酶2（PDE2）相关的中枢神经系统疾病。本发明还涉及使用此类化合物治疗神经和精神疾病，如精神分裂症、精神病、帕金森病、帕金森病痴呆（PDD）或亨廷顿病，以及与纹状体功能低下或基底节功能障碍相关的疾病。
• 6-ALKYL DIHYDROPYRAZOLOPYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3302484A1

  公开（公告）日：2018-04-11
• [EN] 6-ALKYL DIHYDROPYRAZOLOPYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS 6-ALKYL DIHYDROPYRAZOLOPYRIMIDINONE UTILISÉS COMME INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2016196071A1

  公开（公告）日：2016-12-08

  The present invention is directed to 6-alkyl dihydropyrazolopyrimidinone compounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.
• [EN] 6-ALKYL DIHYDROPYRAZOLOPYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS 6-ALKYLE DIHYDROPYRAZOLOPYRIMIDINONE UTILISÉS EN TANT QU'INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2016191935A1

  公开（公告）日：2016-12-08

  The present invention is directed to 6-alkyl dihydropyrazolopyrimidinone compounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.