2,5-二氨基嘧啶 | 22715-27-1

• 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: 2,5-二氨基嘧啶
• 英文名称: pyrimidine-2,5-diamine
• 英文别名: 2,5-diaminopyrimidine；2,5-Diamino-pyrimidin
• CAS: 22715-27-1
• 化学式: C₄H₆N₄
• mdl: MFCD00129726
• 分子量: 110.118
• InChiKey: DNACGYGXUFTEHO-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  401.7±37.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  8
• 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：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090
• 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：
  应储存在室温、避光且处于惰性气体环境之中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Pyrimidine-2,5-diamine
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: Pyrimidine-2,5-diamine
CAS number: 22715-27-1

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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.
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: C4H6N4
Molecular weight: 110.1

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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

反应信息

• 作为反应物：
  描述：

  2,5-二氨基嘧啶 以90%的产率得到
  参考文献：
  名称：

  KRCHNAK V.; ARNOLD Z., COLLECT. CZECH. CHEM. COMMUNS , 1975, 40, NO 5, 1396-1402

  摘要：

  DOI：
• 作为产物：
  描述：

  5-phenylazo-pyrimidin-2-ylamine 在 1,4-二氧六环 、 镍 作用下， 生成 2,5-二氨基嘧啶
  参考文献：
  名称：

  Hensel, Festschr. C. Wurster S. 135, 139

  摘要：

  DOI：

文献信息

• [EN] INHIBITORS OF HEPATITIS C VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2010111483A1

  公开（公告）日：2010-09-30

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种公式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20190127365A1

  公开（公告）日：2019-05-02

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种具有式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• Therapeutic quinazoline derivatives
  申请人：AstraZeneca AB

  公开号：US07235559B1

  公开（公告）日：2007-06-26

  A compound of formula (I) or a salt, ester, amide or prodrug thereof; where X is O, or S, S(O), S(O)2 or NR6 where R6 is hydrogen of C1-6alkyl; R5 is an optionally substituted 6-membered aromatic ring containing at least one nitrogen atom, and R1, R2, R3, R4 are independently selected from halogeno, cyano, nitro, C1-3alkylsulphanyl, —N(OH)R7— (wherein R7 is hydrogen, or C1-3alkyl), or R9X1— (wherein X1 represents a direct bond, —O—, —CH2—, —OC(O), —C(O)—, —S—, —SO—, —SO2—, —NR10C(O)—, —C(O)NR11—, —SO2NR12—, —NR13SO2— or NR14— (wherein R10, R11, R12, R13 and R14 each independently represents hydrogen, C1-3alkyl or C1-3alkoxyC2-3alkyl), and R9 is hydrogen, optionally substituted hydrocarbyl, optionally substituted heterocyclyl or optionally substituted alkoxy; provided that at least one of R2 or R3 is other than hydrogen. These compounds inhibit aurora 2 kinase and are useful in the preparation of medicaments for the treatment of proliferative disease such as cancer.

  化合物的化学式（I）或其盐、酯、酰胺或前药；其中X为O、或S、S（O）、S（O）2或NR6，其中R6为氢或C1-6烷基；R5为含有至少一个氮原子的可选择取代的6-成员芳香环，而R1、R2、R3、R4分别独立地选自卤素、氰基、硝基、C1-3烷基硫基、—N（OH）R7—（其中R7为氢或C1-3烷基）、或R9X1—（其中X1代表直接键、—O—、—CH2—、—OC（O）—、—C（O）—、—S—、—SO—、—SO2—、—NR10C（O）—、—C（O）NR11—、—SO2NR12—、—NR13SO2—或NR14—（其中R10、R11、R12、R13和R14各自独立地代表氢、C1-3烷基或C1-3烷氧基C2-3烷基），而R9为氢、可选择取代的烃基、可选择取代的杂环烷基或可选择取代的烷氧基；但要求R2或R3中至少有一个不是氢。这些化合物抑制aurora 2激酶，并且在制备用于治疗增殖性疾病如癌症的药物方面是有用的。
• Sulfonamido pyrimidines
  申请人：AMERICAN CYANAMID CO

  公开号：US02430439A1

  公开（公告）日：1947-11-04

  555,865. Sulphonamido pyrimidines. AMERICAN CYANAMID CO. March 8, 1941, Nos. 3174 and 3175. Convention dates, March 1, 1940 and Oct. 15, 1940. Samples furnished. [Class 2 (iii)] p-Substituted benzene-sulphonamido-pyrimidenes are made by reacting a benzene-sulphonyl halide, e.g. a chloride substituted in the para position by an amino group or a group convertible thereto by hydrolysis, reduction or by reaction with ammonia or an amine such as an acylamino, nitro, halogen or azo group, with an amino-pyrimidine. The products are of the general formula where R is a halogen, nitro, azo, amino or substituted amino group, e.g. alkylamino, arylamino, aralkylamino, acylamino or monoaldose amino, X is H, an alkyl group or a metal, Py is a pyrimidine substituted or unsubstituted and n is a small integer. The mono-aldose amino compounds are'made from the corresponding amino compounds by reaction with a mono aldose sugar such as galactose or glucose preferably in a solvent such as ethanol. Free hydrogen halide obtained during the reaction with a sulphonyl halide is removed by effecting the reaction in a basic medium, e.g. aqueous sodium hydroxide, triethylamine and pyridine and solvents, e.g. dioxane, acetone and benzene are specified. Alkali metal or heavy metal, e.g. gold, lead, copper and iron, salts of the products are also described. Examples describe the preparation of the following compounds by the above methods (1) 5-(N<;SP>;4<;/SP>;- acetylsulphanilamido) - 2, 4 - dihydroxy-, (2) 5 - (sulphanilamido) - 2, 4 - dihydroxy-, (3) 5 - (p - nitrobenzene sulphonamido) - 2, 4 - dihydroxy-, (4) 5 - (N<;SP>;4<;/SP>; -acetylsulphanil - - amido)-, (5) 5 - (sulphanilamido)-, (6) 4 - (p - nitrobenzenesulphonamido)-, (7) and (9) 4 - (sulphanilamido)-, (8) 4 - (N<;SP>;4<;/SP>; - acetyl - sulphanilamido)-, (10) 2 - (p - nitrobenzene - sulphonamido)-, (11) and (13) 2 - (sulphanil - amido)-, (12) 2 - (N<;SP>;4<;/SP>; - acetylsulphanilamido) -, (14) 4 - p - nitrobenzenesulphonamido 2 - methoxy-, (15) 4 - sulphanilamido - 2 - methoxy-, (16) 2 - (p - nitrobenzene - sulphon - amido) 4 - methoxy-, (17) 2 - sulphanilamido- 4 - methoxy-, (18) 2 - (p - nitrobenzene - sulphonamido) - 4, 6 - dimethyl-, (19) 2 - sulphanlamido - 4, 6 - dimethyl-, (20) 2 - N<;SP>;1<;/SP>; - methyl - sulphanilamido-, (21) 4 - p - chloro - benzene - sulphamido-, (this pyrimidine may be reacted with ammonia or amines, e.g. methylamine, aniline or benzyl amine to yield the corresponding substituted 4-N<;SP>;4<;/SP>; pyrimidine), (22) azobenzene - p -, p<;SP>;1<;/SP>; - (di - 2 - sulphon - amido)-, (23) 5 - (N<;SP>;4<;/SP>; - acetylsulphanilamido) - 2 - acetylamino-, (24) 5 - sulphanilamido - 2 - amino, (25) 5 - (p - nitrobenzenesulphonamido) - 2 - methoxy-, (26) 5 - sulphanilamido - 2. - methoxy-, (27) 2 - (N<;SP>;4<;/SP>; - acetylsulphanilamido) - 4 - ethoxy,- (28) 2 - sulphanilamido - 4 - ethoxy, (29) 2, 5 - di (p - nitrobenzene - sulphonamido)-, (30) 2, 5 - disulphanilamido-, (31) 2 - (p - nitrobenzene - sulphonamido) - 5 - chloro-, (32) 2 - sulphanilamido - 5 - chloro-, (33) sodium salt of 2 - sulphanilamido-, (34) copper salt of 2 - sulphanilamido-, (35) the glucose derivative of 2-sulphanilamido- and (36) 2-(N<;SP>;4<;/SP>;-benzylsulphanilamido)-pyrimidine. Examples (35) and (36) relate to two typical samples which have been furnished. The Specification as open to inspection under Sect. 91 states that in some cases the products may also be made by reacting a halogen substituted pyrimidine with an N<;SP>;4<;/SP>;-acylsulphanilamide in the presence of an alkali with subsequent hydrolysis of the acyl group. In examples (23) N<;SP>;4<;/SP>;-acetylsulphanilamide is treated with 2-chloro-4, 6-dimethylpyrimidine in the presence of potassium carbonate and copper powder to yield 2-N<;SP>;4<;/SP>;-acetylsulphanilamido-4, 6-dimethyl pyrimidine which is hydrolysed to the free amine, (24) 2-sulphanilamidopyrimidine is diazotized and coupled with 7-acetylamino-1-hydroxynaphthalene-3, 6-disulphonic acid to yield 4<;SP>;1<;/SP>;-(N-(2-pyrimidyl) sulphonamido) - 2 - azo - 7 - acetylamino - 1 - hydroxynaphthalene - 3, 6 - disulphonic acid and in (29) 2-(N<;SP>;4<;/SP>;-acetylsulphanilamido)-4- methyl - pyrimidine and (30) 2 - sulphanil - amido - 4 - methylpyrimidine are made by methods described above. This subjectmatter does not appear in the Specification as accepted.

  555,865. 磺胺基嘧啶。美国氰胺公司。1941年3月8日，编号3174和3175。公约日期，1940年3月1日和1940年10月15日。提供样本。[2类（iii）] p-取代苯磺酰氨基嘧啶通过将苯磺酰卤化物（例如，在对位由氨基或可通过水解、还原或与氨或胺（如酰氨基，硝基，卤素或偶氮基）反应转化的基团取代的氯化物）与氨基嘧啶反应制备。产品的一般公式如下，其中R是卤素，硝基，偶氮，氨基或取代氨基，例如烷基氨基，芳基氨基，芳基烷基氨基，酰胺基或单醛氨基，X是H，烷基基团或金属，Py是取代或未取代的嘧啶，n是小整数。单醛氨基化合物通过与单醛糖（例如半乳糖或葡萄糖）反应制备相应的氨基化合物而制备，最好在乙醇等溶剂中。在与苯磺酰卤化物反应过程中产生的游离氢卤酸通过在碱性介质中进行反应（例如水杨酸钠，三乙胺和吡啶）和指定的溶剂（例如二噁英，丙酮和苯）中除去。还描述了产品的碱金属或重金属（例如金，铅，铜和铁）盐。示例描述了通过上述方法制备以下化合物（1）5-（N <; SP>; 4 <;/ SP>; -乙酰磺胺基） - 2,4-二羟基-，（2）5-（磺胺基）- 2,4-二羟基-，（3）5-（对-硝基苯磺胺基）- 2,4-二羟基-，（4）5-（N <; SP>; 4 <;/ SP>; -乙酰磺胺基）-，（5）5-（磺胺基）-，（6）4-（对-硝基苯磺胺基）-，（7）和（9）4-（磺胺基）-，（8）4-（N <; SP>; 4 <;/ SP>; -乙酰-磺胺基）-，（10）2-（对-硝基苯-磺胺基）-，（11）和（13）2-（磺胺-氨基）-，（12）2-（N <; SP>; 4 <;/ SP>; -乙酰磺胺基）-，（14）4-对-硝基苯磺胺基2-甲氧基-，（15）4-磺胺基-2-甲氧基-，（16）2-（对-硝基苯磺胺基）-4-甲氧基-，（17）2-磺胺基-4-甲氧基-，（18）2-（对-硝基苯磺胺基）-4,6-二甲基-，（19）2-磺胺基-4,6-二甲基-，（20）2-N <; SP>; 1 <;/ SP>; -甲基-磺胺基-，（21）4-对-氯苯-磺胺基-，（该嘧啶可以与氨或胺（例如甲胺，苯胺或苄胺）反应，生成相应的取代4-N <; SP>; 4 <;/ SP>; 嘧啶），（22）偶氮苯-对-，p <; SP>; 1 <;/ SP>; -（二-2-磺-氨基）-，（23）5-（N <; SP>; 4 <;/ SP>; -乙酰磺胺基）-2-乙酰氨基-，（24）5-磺胺基-2-氨基，（25）5-（对-硝基苯磺胺基）-2-甲氧基-，（26）5-磺胺基-2. -甲氧基-，（27）2-（N <; SP>; 4 <;/ SP>; -乙酰磺胺基）-4-乙氧基-，（28）2-磺胺基-4-乙氧基，（29）2,5-二（对-硝基苯-磺胺基）-，（30）2,5-二磺胺基-，（31）2-（对-硝基苯-磺胺基）-5-氯-，（32）2-磺胺基-5-氯-，（33）2-磺胺基-的钠盐，（34）2-磺胺基-的铜盐，（35）2-磺胺基-的葡萄糖衍生物和（36）2-（N <; SP>; 4 <;/ SP>; -苄基磺胺基）-嘧啶。示例（35）和（36）涉及
• Bis-aryl amide compounds and methods of use
  申请人：Dimauro F. Erin

  公开号：US20070072862A1

  公开（公告）日：2007-03-29

  The present invention comprises a new class of compounds useful for the prophylaxis and treatment of protein kinase mediated diseases, including autoimmune disease and inflammation. In one embodiment, the compounds have a general Formula I wherein A 1 , A 2 , A 3 , A 4 , L, R 1 , R 2 and R 3 are defined herein. The invention also comprises pharmaceutical compositions including one or more compounds of the present invention, methods of use such as treatment of Lck and/or c-Kit kinase mediated diseases by administering the compounds of the invention, or compositions including one or more compounds of the invention, and intermediates and processes useful for the preparation of compounds of the present invention.

  本发明涵盖了一类新的化合物，用于预防和治疗蛋白激酶介导的疾病，包括自身免疫疾病和炎症。在一个实施例中，这些化合物具有一般的化学式I，其中A1、A2、A3、A4、L、R1、R2和R3在此处定义。本发明还涵盖了包括本发明的一种或多种化合物的药物组合物，使用方法如通过给予本发明的化合物治疗Lck和/或c-Kit激酶介导的疾病，或包括本发明的一种或多种化合物的组合物，以及用于制备本发明化合物的中间体和方法。

表征谱图