4-氯-7-甲基吡咯并[2,3-D]嘧啶 | 7781-10-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 中文名称: 4-氯-7-甲基吡咯并[2,3-D]嘧啶
• 中文别名: 4-氯-7-甲基-7H-吡咯并[2,3-D]嘧啶；4-氯-7-甲基吡咯并2,3-D嘧啶
• 英文名称: 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 4-chloro-7-methylpyrrolo[2,3-d]pyrimidine；4-Chlor-7-methyl-7H-pyrrolo<2,3-d>pyrimidin
• CAS: 7781-10-4
• 化学式: C₇H₆ClN₃
• mdl: MFCD00619245
• 分子量: 167.598
• InChiKey: BJGDLOLPALCTJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  301.5±22.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  T
• 安全说明：
  S45
• 危险类别码：
  R25
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Chloro-7-methyl-7h-pyrrolo[2,3-d]pyrimidine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Chloro-7-methyl-7h-pyrrolo[2,3-d]pyrimidine
CAS number: 7781-10-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H6ClN3
Molecular weight: 167.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (4-Chloro-7-methyl-7h-pyrrolo[2,3-d]pyrimidine)

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

4-氯-7-甲基吡咯并[2,3-D]嘧啶是一种用于合成的有机中间体。

制备方法

将500 mg（3.26 mmol，1.00 当量）4-氯-7H-吡咯并[2,3-d]嘧啶溶解于5 mL DMF 中。加入1.59 g（4.88 mmol，1.50 当量）碳酸铯，在室温下搅拌10 分钟后，再加入405.37 μL（6.51 mmol，2.00 当量）碘甲烷。在室温下继续搅拌反应混合物1 小时。将反应混合物过滤，并用乙酸乙酯洗涤固体产物。滤液用水和盐水洗涤后，使用硫酸镁干燥并过滤，浓缩得到的黄色粉末即为4-氯-7-甲基吡咯并[2,3-D]嘧啶（540 mg，收率99%）。核磁共振氢谱（1H NMR，DMSO-d6，300 MHz）显示：δ 8.65 (s, 1H)；7.74 (d，J=3.5 Hz, 1H)；6.64 (d，J=3.5 Hz, 1H)；3.86 (s, 3H)。

反应信息

• 作为反应物：
  描述：

  4-氯-7-甲基吡咯并[2,3-D]嘧啶 在 氨 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以67.7%的产率得到7-甲基-7H-吡咯并[2,3-d]嘧啶-4-胺
  参考文献：
  名称：

  Seela, Frank; Bussmann, Werner, Chemische Berichte, 1981, vol. 114, # 6, p. 2056 - 2063

  摘要：

  DOI：
• 作为产物：
  描述：

  7-甲基-3H-吡咯并[3,2-e]嘧啶-4-酮 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 4-氯-7-甲基吡咯并[2,3-D]嘧啶
  参考文献：
  名称：

  Discovery of a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine and a 1-aryloxyisoquinoline series of TRPA1 antagonists

  摘要：

  A series of TRPA1 antagonists is described having a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine or a 1-aryloxyisoquinoline scaffold. These compounds have high ligand efficiency and favorable physical properties and may thus serve as scaffolds for further optimization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.045

文献信息

• [EN] BIARYL KINASE INHIBITORS<br/>[FR] INHIBITEURS BIARYLES DE KINASES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2017059080A1

  公开（公告）日：2017-04-06

  The present disclosure is directed to biaryl compounds of formula (I) which can inhibit AAKl (adaptor associated kinase 1), compositions comprising such compounds and their use for treating e.g. pain, Alzheimer's disease, Parkinson's disease and schizophrenia.

  本公开涉及公式（I）的联苯化合物，可以抑制AAK1（适配器相关激酶1），包括这种化合物的组合物以及它们用于治疗疼痛、阿尔茨海默病、帕金森病和精神分裂症等的用途。
• N-(HETERO)ARYL-PYRROLIDINE DERIVATIVES OF PYRAZOL-4-YL-PYRROLO[2,3-d]PYRIMIDINES AND PYRROL-3-YL-PYRROLO[2,3-d]PYRIMIDINES AS JANUS KINASE INHIBITORS
  申请人：Rodgers James D.

  公开号：US20100298334A1

  公开（公告）日：2010-11-25

  The present invention relates to N-(hetero)aryl-pyrrolidine derivatives of Formula I: which are JAK inhibitors, such as selective JAK1 inhibitors, useful in the treatment of JAK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.

  本发明涉及式I的N-(杂)芳基吡咯烷衍生物： 这些是JAK抑制剂，如选择性JAK1抑制剂，在治疗JAK相关疾病方面具有用处，例如炎症和自身免疫性疾病，以及癌症。
• Expanding the Diversity of Allosteric Bcr-Abl Inhibitors
  作者：Xianming Deng、Barun Okram、Qiang Ding、Jianming Zhang、Yongmun Choi、Francisco J. Adrián、Amy Wojciechowski、Guobao Zhang、Jianwei Che、Badry Bursulaya、Sandra W. Cowan-Jacob、Gabriele Rummel、Taebo Sim、Nathanael S. Gray

  DOI：10.1021/jm100555f

  日期：2010.10.14

  Inhibition of Bcr-Abl kinase activity by imatinib for the treatment of chronic myeloid leukemia (CML) currently serves as the paradigm for targeting dominant oncogenes with small molecules. We recently reported the discovery of GNF-2 (1) and GNF-5 (2) as selective non-ATP competitive inhibitors of cellular Bcr-Abl kinase activity that target the myristate binding site. Here, we used cell-based structure−activity

  伊马替尼对 Bcr-Abl 激酶活性的抑制用于治疗慢性粒细胞白血病 (CML)，目前作为用小分子靶向显性癌基因的范例。我们最近报道了 GNF-2 ( 1 ) 和 GNF-5 ( 2 ) 作为靶向肉豆蔻酸结合位点的细胞 Bcr-Abl 激酶活性的选择性非 ATP 竞争性抑制剂的发现。在这里，我们使用基于细胞的结构-活性关系来指导能够与肉豆蔻酸酯结合位点结合的配体的优化和多样化，并使基于 Abl-化合物1的发现合理化共晶。我们阐明了获得针对 Bcr-Abl 转化细胞的强效抗增殖活性所需的结构-活性关系，并报告了新化合物（5g、5h、6a、14d和21j-I）的发现，这些化合物显示出改进的效力或药理特性。这项工作表明，多种结构可以有效地靶向 Bcr-Abl 肉豆蔻酸酯结合位点，并为开发可靶向该结合位点的药物提供了新的线索。
• [EN] IMIDAZOLIDINONE DERIVATIVES AS INHIBITORS OF PERK<br/>[FR] DÉRIVÉS D'IMIDAZOLIDINONE COMME INHIBITEURS DE PERK
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO 2) LTD

  公开号：WO2017046739A1

  公开（公告）日：2017-03-23

  The invention is directed to substituted imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I (I) wherein R1, R2, R3, R4, R5, R6, R7, X, Y1, Y2 and Z are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes, as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt-Jakob Disease, fatal familial insomnia, Gerstmann-Sträussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  这项发明涉及取代咪唑烷酮衍生物。具体而言，该发明涉及根据式I（I）中R1、R2、R3、R4、R5、R6、R7、X、Y1、Y2和Z所定义的化合物。该发明的化合物是PERK的抑制剂，可用于治疗癌症、癌前综合征、阿尔茨海默病、神经病性疼痛、脊髓损伤、创伤性脑损伤、缺血性中风、中风、帕金森病、糖尿病、代谢综合征、代谢紊乱、亨廷顿病、克雅氏病、致命性家族性失眠、格斯特曼-施特劳斯勒-谢因克症候群及相关朊蛋白病、肌萎缩侧索硬化、进行性核上性麻痹、心肌梗死、心血管疾病、炎症、器官纤维化、肝脏慢性和急性疾病、脂肪肝病、肝脂肪变性、肝纤维化、肺部慢性和急性疾病、肺纤维化、肾脏慢性和急性疾病、肾脏纤维化、慢性创伤性脑病（CTE）、神经退行性疾病、痴呆症、额颞叶痴呆症、tau蛋白病、皮克氏病、尼曼-皮克氏病、淀粉样变性、认知障碍、动脉粥样硬化、眼部疾病、心律失常、器官移植以及器官移植用途中的运输。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物抑制PERK活性和治疗相关疾病的方法。
• [EN] NEW PIPERIDINYL DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS DE PIPÉRIDINYLE, PROCÉDÉ DE PRÉPARATION DE CEUX-CI ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2017212012A1

  公开（公告）日：2017-12-14

  Compounds of formula (I) wherein R1, R2, R3, n and W are as defined in the description. Medicaments.

  式（I）中R1、R2、R3、n和W的化合物如描述中所定义。药物。