(5-溴嘧啶-2-基)氨基甲酸叔丁酯 | 883231-23-0

• 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 - 二嗪类
• 中文名称: (5-溴嘧啶-2-基)氨基甲酸叔丁酯
• 中文别名: 5-溴-n-boc-嘧啶-2-胺
• 英文名称: tert-butyl (5-bromopyrimidin-2-yl)carbamate
• 英文别名: tert-butyl N-(5-bromopyrimidin-2-yl)carbamate
• CAS: 883231-23-0
• 化学式: C₉H₁₂BrN₃O₂
• 分子量: 274.117
• InChiKey: MQQCCIJHZDEZBW-UHFFFAOYSA-N

物化性质

• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温条件下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(N-BOC-Amino)-5-bromopyrimidine
Synonyms: tert-Butyl 5-bromopyrimidin-2-ylcarbamate

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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: 2-(N-BOC-Amino)-5-bromopyrimidine
CAS number: 883231-23-0

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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.
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: C9H12BrN3O2
Molecular weight: 274.1

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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, hydrogen bromide.

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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

反应信息

• 作为反应物：
  描述：

  (5-溴嘧啶-2-基)氨基甲酸叔丁酯 在 bis-triphenylphosphine-palladium(II) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Discovery of 2-(2-aminopyrimidin-5-yl)-4-morpholino- N -(pyridin-3-yl)quinazolin-7-amines as novel PI3K/mTOR inhibitors and anticancer agents

  摘要：

  In this study, a series of novel 7 or 8-substituted 4-morpholine-quinazoline derivatives was designed and synthesized. Their PI3K alpha inhibitory activities, antiproliferative activities against seven cancer cell lines, namely, PC-3, DU145, MCF-7, BT474, SK-BR-3, U937 and A431, were evaluated in vitro. Compound 17f proved to be a potential drug candidate with high PI3K alpha inhibition activity (IC50 = 4.2 nM) and good antiproliferative activity. Compound 17f was also tested for its inhibitory activities against other kinases, such as PI3K beta, PI3K gamma, PI3K delta and mTOR, its effects on p-Akt (S473) and cell cycle. These results suggested that compound 17f could significantly inhibit the PI3K/Akt/mTOR pathway as a potent PI3K inhibitor and anticancer agent. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.038
• 作为产物：
  描述：

  2-[双(叔丁氧羰基)氨基]-5-溴嘧啶 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (5-溴嘧啶-2-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  PROCESS FOR MAKING THIENOPYRIMIDINE COMPOUNDS

  摘要：

  制备双重mTOR/PI3K抑制剂GDC-0980的工艺方法，化学名称为(S)-1-(4-((2-(2-氨基嘧啶-5-基)-7-甲基-4-吗啉基噻吩[3,2-d]嘧啶-6-基)甲基)哌嗪-1-基)-2-羟基丙酮-1-酮，具有以下结构和立体异构体、几何异构体、互变异构体和其药用可接受盐。

  公开号：

  US20140100366A1

文献信息

• [EN] CERTAIN PROTEIN KINASE INHIBITORS<br/>[FR] INHIBITEURS DE CERTAINES PROTÉINES KINASES
  申请人：CHONGQING FOCHON PHARMACEUTICAL CO LTD

  公开号：WO2017114351A1

  公开（公告）日：2017-07-06

  Provided are certain CDK4/6 inhibitors, pharmaceutical compositions, and medthods of use thereof.

  提供了某些CDK4/6抑制剂、药物组成和使用方法。
• Metallaphotoredox Difluoromethylation of Aryl Bromides
  作者：Vlad Bacauanu、Sébastien Cardinal、Motoshi Yamauchi、Masaru Kondo、David F. Fernández、Richard Remy、David W. C. MacMillan

  DOI：10.1002/anie.201807629

  日期：2018.9.17

  strategy for the difluoromethylation of aryl bromides by metallaphotoredox catalysis. Bromodifluoromethane, a simple and commercially available alkyl halide, is harnessed as an effective source of difluoromethyl radical by silyl‐radical‐mediated halogen abstraction. The merger of this fluoroalkyl electrophile activation pathway with a dual nickel/photoredox catalytic platform enables the difluoromethylation

  在此，我们报告了一种通过金属光氧化还原催化芳基溴二氟甲基化的方便且广泛适用的策略。溴二氟甲烷是一种简单且市售的烷基卤化物，通过甲硅烷基介导的卤素抽象，可将其用作二氟甲基自由基的有效来源。这种氟烷基亲电试剂活化途径与双镍/光氧化还原催化平台的合并使得能够在温和条件下对多种芳基和杂芳基溴化物进行二氟甲基化。该过程的实用性在几种药物类似物的后期功能化中得到了体现。
• A scaffold hopping strategy to generate new aryl-2-amino pyrimidine MRSA biofilm inhibitors
  作者：Alexander W. Weig、Samantha L. Barlock、Patrick M. O'Connor、Orry M. Marciano、Richard Smith、Robert K. Ernst、Roberta J. Melander、Christian Melander

  DOI：10.1039/d0md00238k

  日期：——

  Infections that stem from bacterial biofilms are difficult to eradicate. Within a biofilm state, bacteria are upwards of 1000-fold more resistant to conventional antibiotics, necessitating the development of alternative approaches to treat biofilm-based infections. One such approach is the development of small molecule adjuvants that can inhibit/disrupt bacterial biofilms. When such molecules are paired

  源于细菌生物膜的感染很难根除。在生物膜状态下，细菌对传统抗生素的抵抗力提高了 1000 倍以上，因此需要开发替代方法来治疗基于生物膜的感染。一种这样的方法是开发可以抑制/破坏细菌生物膜的小分子佐剂。当此类分子与常规抗生素配对时，这些双重治疗提供了一种根除基于生物膜的感染的组合方法。以前，我们已经证明含有 2-氨基嘧啶 (2-AP) 或 2-氨基咪唑 (2-AI) 杂环的小分子是有效的抗生物膜剂。在此，我们现在报告了一种支架跳跃策略，以产生新的芳基 2-AP 类似物，通过耐甲氧西林抑制生物膜形成金黄色葡萄球菌(MRSA)。这些分子还抑制了耐粘菌素肺炎克雷伯菌的粘菌素耐药性，将最低抑菌浓度 (MIC) 降低了 32 倍。
• SUBSTITUTED PHENETHYLAMINES
  申请人：Gant Thomas G.

  公开号：US20100222257A1

  公开（公告）日：2010-09-02

  Disclosed herein are substituted phenethylamine alpha adrenergic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

  本文披露了一种公式为I的取代苯乙胺α肾上腺素受体调节剂，其制备方法、制药组合物及使用方法。
• Process for making thienopyrimidine compounds
  申请人：Genentech, Inc.

  公开号：US08895729B2

  公开（公告）日：2014-11-25

  Process methods for making the dual mTOR/PI3K inhibitor GDC-0980, named as (S)-1-(4-((2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one, having the structure: and stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof.

  制备双重mTOR/PI3K抑制剂GDC-0980的流程方法，命名为(S)-1-(4-((2-(2-氨基嘧啶-5-基)-7-甲基-4-吗啡基噻吩[3,2-d]嘧啶-6-基)甲基)哌嗪-1-基)-2-羟基丙酮，其结构如下图所示，并包括立体异构体、几何异构体、互变异构体和其药学上可接受的盐。