2-氨基-5-溴-4-羟基嘧啶 | 61937-71-1

• 物质功能分类: 医药中间体 - 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: 2-氨基-5-溴-4-羟基嘧啶
• 英文名称: 2-amino-5-bromo-3H-pyrimidin-4-one
• 英文别名: 2-amino-5-bromo-4-hydroxypyrimidine；5-Brom-2-amino-4-hydroxy-pyrimidin；5-Brom-2-amino-pyrimidin；5-Brom-isocytosin；2-Amino-5-bromo-4-pyrimidinol；2-amino-5-bromo-1H-pyrimidin-6-one
• CAS: 61937-71-1
• 化学式: C₄H₄BrN₃O
• 分子量: 189.999
• InChiKey: PDLZQTZTKDRRAP-UHFFFAOYSA-N

物化性质

• 熔点：
  284-285°
• 密度：
  2.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-5-bromo-4-pyrimidinol
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: 2-Amino-5-bromo-4-pyrimidinol
CAS number: 61937-71-1

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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: C4H4BrN3O
Molecular weight: 190.0

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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：

  2-氨基-5-溴-4-羟基嘧啶 、 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine 反应 0.17h， 以41%的产率得到5-[(3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]isocytosine
  参考文献：
  名称：

  Synthesis of 1′-aza-C-nucleosides from (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol

  摘要：

  Pyrimidine 1'-aza-C-nucleosides are synthesised by the fusion of 5-bromouracil, 5-bromocytosine and 5-bromoisocytosine with (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol in 40-41% yield. A homologue of 1'-aza-Psi -uridine is obtained in a Mannich reaction in 65% yield by treatment of the azasugar, paraformaldehyde and uracil. N-Alkylation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol with 6-chloromethyluracil gives the 6-regioisomeric homologue. (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol is synthesised in 25% overall yield from diacetone-D-glucose via 3-C-(azidomethyl)-3-deoxy-D-allose which is subjected to an intramolecular reductive amino alkylation reaction to give (3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol followed by Fmoc protection, oxidative cleavage of the triol group with further reduction of the obtained aldehyde and subsequent deprotection of the nitrogen atom. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00920-6
• 作为产物：
  描述：

  异胞嘧啶 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 2-氨基-5-溴-4-羟基嘧啶
  参考文献：
  名称：

  Nitrogen-containing heterocyclic compounds, their production and use

  摘要：

  该式的化合物： 其中A和D中的一个是N，另一个是C，或者两者都是N；B是N或C；m为0-3；R1、R2和R3分别是(i) H或(ii) 通过C、N、O或S结合的基团；R4是通过C结合的基团；R5是H或通过C或O结合的基团；R6是H或通过C结合的基团；R7是可能被取代的同源或异源环基团；或其盐具有出色的促性腺激素释放激素拮抗活性，并且可用作性激素依赖性疾病的预防或治疗剂等。

  公开号：

  US06194419B1

文献信息

• 嘧啶及其变体、及其用途
  申请人：传入制药公司

  公开号：CN108779119B

  公开（公告）日：2022-02-08

  本公开提供了式1的嘧啶化合物及其用途，例如用于潜在治疗与P2X嘌呤受体相关的疾病。在某些方面中，本公开提供了可用于例如潜在治疗内脏器官、心血管和疼痛相关的疾病、病症和紊乱的P2X3和/或P2X2/3拮抗剂。
• An improved synthesis of 2-amino-5-[(4-chlorophenyl)thio]-4-morpholinopyrimidine (BW 394U) - A potential antisenility agent
  作者：Vicente Samano、Virgil L. Styles、Joseph H. Chan

  DOI：10.1002/jhet.5570370131

  日期：2000.1

  This paper describes the synthesis of 2-amino-5-[(4-chlorophenyl)thio]-4-morpholinopyrimidine (BW 394U, compound 4), a potential antisenility agent. The key intermediates 3a/3b were obtained from an in situ-generated Vilsmeier-Haack reagent that simultaneously protected the 2-amino group prior to further manipulations. Displacement of the chloro group in 3a gave 4 in 40% yield and 4-dimethylamino analogue

  本文介绍了一种潜在的抗衰老剂2-氨基-5-[（4-氯苯基）硫代] -4-吗啉基嘧啶（BW 394U，化合物4）的合成。关键中间体3a / 3b获自原位产生的Vilsmeier-Haack试剂，该试剂在进一步操作之前同时保护了2-氨基。在氯基团的位移3A得到4，收率40％和4-二甲基氨基类似物5.然而，位移3b中与吗啉，接着用碱水溶液，得到4，74％收率。
• [EN] PYRIMIDINES AND VARIANTS THEREOF, AND USES THEREFOR<br/>[FR] PYRIMIDINES ET VARIANTES DE CELLES-CI, ET LEURS UTILISATIONS
  申请人：AFFERENT PHARMACEUTICALS INC

  公开号：WO2017160569A1

  公开（公告）日：2017-09-21

  The present disclosure provides pyrimidine compounds and uses thereof, for example, for the treatment of diseases associated with P2X purinergic receptors. In certain aspects, the present disclosure provides P2X3 and/or P2X2/3 antagonists which are useful, for example, for the treatment of visceral organ, cardiovascular and pain-related diseases, conditions and disorders.

  本公开提供嘧啶化合物及其用途，例如用于治疗与P2X嘌呤受体相关的疾病。在某些方面，本公开提供P2X3和/或P2X2/3拮抗剂，这些拮抗剂可用于治疗内脏器官、心血管和与疼痛相关的疾病、症状和障碍。
• Synthetic Routes to a Series of Proximal and Distal 2′-Deoxy Fleximers
  作者：Katherine Seley-Radtke、Orrette Wauchope、Melvin Velasquez

  DOI：10.1055/s-0032-1316791

  日期：——

  Two series of innovative 2'-deoxy nucleoside analogues have been designed where the nucleobase has been split into its imidazole and pyrimidine subunits. This structural modification serves to introduce flexibility into the nucleobase scaffold while still retaining the elements required for recognition. The synthetic efforts to realize these analogues are described within.
• Johnson; Johns, American Chemical Journal, 1905, vol. 34, p. 564
  作者：Johnson、Johns

  DOI：——

  日期：——