7H-吡咯并[2,3-D]嘧啶 | 271-70-5

• 物质功能分类: 化学试剂 - 有机试剂 - 芳烃
• 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: 7H-吡咯并[2,3-D]嘧啶
• 中文别名: 7H-吡咯[3,2-D]嘧啶；吡咯[2,3-D]嘧啶；1H-吡咯并(2,3-d)嘧啶；7H-吡咯并[2,3-d]嘧啶；1H-吡咯并[2,3-D]嘧啶；1H-吡咯并[2,3-d]嘧啶
• 英文名称: 7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: Pyrrolo<2,3-d>pyrimidin；pyrrolo<2,3-d>pyrimidine
• CAS: 271-70-5
• 化学式: C₆H₅N₃
• mdl: MFCD08234403
• 分子量: 119.126
• InChiKey: JJTNLWSCFYERCK-UHFFFAOYSA-N

物化性质

• 熔点：
  133℃
• 沸点：
  297.9±23.0 °C(Predicted)
• 密度：
  1.38
• 溶解度：
  可溶于氯仿、二氯甲烷、DMSO、甲醇
• 最大波长(λmax)：
  270nm(MeOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 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.

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Section 3. Composition/information on ingredients.
Ingredient name: 7H-Pyrrolo[2,3-d]pyrimidine
CAS number: 271-70-5

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Store in closed vessels, refrigerated.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H5N3
Molecular weight: 119.1

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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.

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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
Non-harzardous for air and ground transportation.

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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

向一个500毫升四颈瓶中加入无水乙醇300 mL和4-氯吡咯并嘧啶12 g，再加入钯炭10 g。在常压下通入氢气还原12小时。反应结束后，在60℃条件下浓缩无水乙醇至较小体积。然后，调节pH值至8～9，加入200 mL纯化水，并降温至5℃搅拌30分钟。过滤后，可得到化合物7H-吡咯并[2,3-D]嘧啶。

反应信息

• 作为反应物：
  描述：

  7H-吡咯并[2,3-D]嘧啶 在 bovine buttermilk xanthine oxidase 作用下， 以 phosphate buffer 为溶剂， 生成 2,4-二羟基吡咯[2,3-d]嘧啶
  参考文献：
  名称：

  Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors

  摘要：

  Thymidine phosphorylase (TP) is over-expressed in various tumour types and plays an important role in tumour angiogenesis, growth, invasion and metastasis. The enzymatic activity of TP is required for the angiogenic effect of TP, therefore, inhibitors of TP are of significant interest in cancer chemotherapy. A series of xanthine oxidase (XO) activated prodrugs of known inhibitors of TP have been designed and synthesized with the ultimate intent of improving tumour selectivity and pharmacokinetic characteristics. These prodrugs were not inhibitors of TP, but were selectively oxidized by XO at C-2 and/or C-4 of the uracil ring moiety to generate the desired TP inhibitor. Molecular modelling of both the TP inhibitors and XO-activated prodrugs rationalized their binding in the active site of the human TP crystal structure. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.07.015
• 作为产物：
  描述：

  4-氯吡咯并嘧啶 在 20% Pd(OH)2 on carbon 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到7H-吡咯并[2,3-D]嘧啶
  参考文献：
  名称：

  AZAINDOLE DERIVATIVES WITH A COMBINATION OF PARTIAL NICOTINIC ACETYL-CHOLINE RECEPTOR AGONISM AND DOPAMINE REUPTAKE INHIBITION

  摘要：

  阿扎因多ール衍生物的公式（I）如下： 其中符号的含义如说明书中所给。这些化合物具有部分尼古丁乙酰胆碱受体激动作用和去甲肾上腺素再摄取抑制作用。本发明还涉及包含这些化合物的药物组合物，制造它们的方法，制造用于其合成的新的中间体的方法，制造组合物的方法以及这些化合物和组合物的用途，例如，用于将它们施用于患者以在尼古丁受体和/或去甲肾上腺素转运体涉及的疾病中实现治疗效果，或者可以通过操纵这些受体来治疗的疾病。

  公开号：

  US20080009514A1
• 作为试剂：
  描述：

  2,4-二氨基-6-羟基嘧啶 、 sodium acetate 、 3-bromo-4-methyl-pentanal 在 7H-吡咯并[2,3-D]嘧啶 、 甲醇 作用下， 以 乙腈 、 水 为溶剂， 反应 16.0h， 以to give 2-amino-5-isopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (3.80 g, 40%)的产率得到2-amino-5-isopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Pyrrolopyrimidines and Related Analogs as HSP90-Inhibitors

  摘要：

  本文描述并证明吡咯并嘧啶及相关类似物作为热休克蛋白90（HSP90）抑制剂在治疗和预防各种HSP90介导的疾病中具有效用，例如增殖性疾病。本文还描述和声明了这些化合物的合成和使用方法。

  公开号：

  US20070173483A1

文献信息

• [EN] AZADECALIN DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'AZADÉCALINE EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK (NO 5) LTD

  公开号：WO2018002848A1

  公开（公告）日：2018-01-04

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, azadecaline derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors, as represented by compounds of Formula (I). These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物影响特性的化合物，其药物组合物和使用方法已列出。具体来说，提供了具有独特抗病毒活性的阿扎德卡林衍生物，作为HIV成熟抑制剂，如化合物(I)的公式所代表的那样。这些化合物对于治疗HIV和艾滋病是有用的。
• IRAK DEGRADERS AND USES THEREOF
  申请人：Kymera Therapeutics, Inc.

  公开号：US20190192668A1

  公开（公告）日：2019-06-27

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。
• BICYCLIC COMPOUNDS HAVING ANTIMITOTIC AND/OR ANTITUMOR ACTIVITY AND METHODS OF USE THEREOF
  申请人：Gangjee Aleem

  公开号：US20100010016A1

  公开（公告）日：2010-01-14

  The present invention provides bicyclic compounds, pharmaceutically acceptable salts, prodrugs, solvates, and hydrates thereof, having antimitotic activity, anti-multidrug resistance activity, such as for example P-glycoprotein inhibition, and antitumor activity, and which inhibit paclitaxel sensitive and resistant tumor cells. Also provided are methods of utilizing these compounds for treating tumor cells and inhibiting mitosis of cancerous cells.

  本发明提供了具有抗有丝分裂活性、抗多药耐药活性（例如P-糖蛋白抑制作用）和抗肿瘤活性的双环化合物、药用可接受盐、前药、溶剂化合物和水合物，其能够抑制紫杉醇敏感和耐药肿瘤细胞。还提供了利用这些化合物治疗肿瘤细胞和抑制癌细胞有丝分裂的方法。
• [EN] PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF<br/>[FR] INHIBITEURS DE LA PRMT5 CONTENANT UNE DIHYDRO- OU TÉTRAHYDRO-ISOQUINOLÉINE ET LEURS UTILISATIONS
  申请人：EPIZYME INC

  公开号：WO2014100730A1

  公开（公告）日：2014-06-26

  Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5- mediated disorders are also described.

  本文描述了式（A）的化合物，其药学上可接受的盐以及药物组合物。本发明的化合物对抑制PRMT5活性是有用的。还描述了利用这些化合物治疗PRMT5介导的疾病的方法。
• PRMT5 INHIBITORS AND USES THEREOF
  申请人：Duncan Kenneth W.

  公开号：US20190083482A1

  公开（公告）日：2019-03-21

  Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

  本文描述了式（I）的化合物，其药学上可接受的盐以及药物组合物。本发明的化合物对抑制PRMT5活性是有用的。还描述了利用这些化合物治疗PRMT5介导的疾病的方法。