2-氨基-4-甲氧基嘧啶 | 155-90-8

• 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-4-甲氧基嘧啶
• 中文别名: 4-甲氧基-2-氨基嘧啶；2-胺基-4-甲氧基吡啶
• 英文名称: 4-methoxypyrimidin-2-amine
• 英文别名: 2-Amino-4-methoxy-pyrimidin；2-amino-4-methoxypyrimidine；4-methoxy-2-aminopyrimidine；4-(methyloxy)-2-pyrimidinamine
• CAS: 155-90-8
• 化学式: C₅H₇N₃O
• 分子量: 125.13
• InChiKey: YNXLSFXQTQKQEF-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  313.1±34.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61
• 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：
  P261
• 危险性描述：
  H302,H315,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4-methoxypyrimidine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-4-methoxypyrimidine
CAS number: 155-90-8

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H7N3O
Molecular weight: 125.1

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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-氨基-4-甲氧基嘧啶 在 sodium amide 、 甲苯 作用下， 生成 benzyl-(4-methoxy-pyrimidin-2-yl)-amine
  参考文献：
  名称：

  Naito et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 348

  摘要：

  DOI：
• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以22 mg的产率得到2-氨基-4-甲氧基嘧啶
  参考文献：
  名称：

  通过焓控制的亲核官能化对嘧啶进行 C2 选择性、官能团发散胺化

  摘要：

  杂芳胺的合成因其在小分子发现中的重要性而一直是有机化学中的一个重要课题。特别是，2-氨基嘧啶代表了一种在生物活性分子中普遍存在的高度特权结构基序，但通过直接功能化引入嘧啶 C2-N 键的一般策略是难以捉摸的。在这里，我们描述了一种用于位点选择性 C-H 官能化的合成平台，该平台提供嘧啶基亚胺盐中间体，然后可以原位转化为各种胺产物。基于机制的试剂设计允许嘧啶的 C2 选择性胺化，开辟了位点选择性杂芳基 C-H 官能化的新范围。

  DOI：

  10.1021/jacs.1c13373

文献信息

• [EN] VIRAL REPLICATION INHIBITORS<br/>[FR] INHIBITEURS DE REPLICATION VIRALE
  申请人：UNIV LEUVEN KATH

  公开号：WO2013045516A1

  公开（公告）日：2013-04-04

  The present invention relates to a series of novel compounds, methods to prevent or treat viral infections in animals by using the novel compounds and to said novel compounds for use as a medicine, more preferably for use as a medicine to treat or prevent viral infections, particularly infections with RNA viruses, more particularly infections with viruses belonging to the family of the Flaviviridae, and yet more particularly infections with the Dengue virus. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the novel compounds, to the compositions or preparations for use as a medicine, more preferably for the prevention or treatment of viral infections. The invention also relates to processes for preparation of the compounds.

  本发明涉及一系列新化合物，通过使用这些新化合物来预防或治疗动物的病毒感染的方法，以及将这些新化合物用作药物，更好地用于治疗或预防病毒感染，特别是感染RNA病毒，更特别是感染属于黄病毒科的病毒，更特别是感染登革病毒。本发明还涉及这些新化合物的药物组合或混合制剂，用作药物的组合或制剂，更好地用于预防或治疗病毒感染。该发明还涉及这些化合物的制备方法。
• Rational Design and Evaluation of 6-(Pyrimidin-2-ylamino)-3,4-dihydroquinoxalin-2(1<i>H</i>)-ones as Polypharmacological Inhibitors of BET and Kinases
  作者：Kaikai Lv、Weicong Chen、Danqi Chen、Jie Mou、Huijie Zhang、Tiantian Fan、Yanlian Li、Danyan Cao、Xin Wang、Lin Chen、Jingkang Shen、Dongsheng Pei、Bing Xiong

  DOI：10.1021/acs.jmedchem.0c00962

  日期：2020.9.10

  proposed a hybrid strategy by incorporating pharmacophores that bind to the acetylated lysine binding pocket of BET proteins with a typical kinase hinge binder to generate novel polypharmacological inhibitors of BET and kinases. Through elaborating the core structure of 6-(pyrimidin-2-ylamino)-3,4-dihydroquinoxalin-2(1H)-one, we demonstrated that this rational design can produce high potent inhibitors of CDK9

  癌症表现出多样的异质性，具有复杂的分子基础，通常具有遗传和表观遗传异常，这对单靶标药物构成了巨大挑战。在当前的工作中，我们提出了一种混合策略，即通过结合具有典型激酶铰链结合剂的BET蛋白的乙酰化赖氨酸结合口袋的药效团，来生成BET和激酶的新型多药理学抑制剂。通过阐述6-（嘧啶-2-基氨基）-3,4-二氢喹喔啉-2（1 H）-one的核心结构，我们证明了这种合理的设计可以产生高效的CDK9和BET蛋白抑制剂。在本系列中，化合物40被确定为具有平衡BRD4活性的潜在先导化合物（IC 50= 12.7 nM）和CDK9（IC 50 = 22.4 nM），以及在小癌细胞板上的良好抗增殖活性。总之，当前的研究提供了一种发现溴结构域和激酶双重抑制剂的新方法，而不仅仅是偶然发现。
• [EN] HETEROCYCLIC COMPOUNDS AS DELTA-5 DESATURASE INHIBITORS AND METHODS OF USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE DELTA-5 DÉSATURASE ET PROCÉDÉS D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2021108404A1

  公开（公告）日：2021-06-03

  The present disclosure provides compounds useful for the inhibition of Delta-5 Desaturase ("D5D"). The compounds have a general Formula (I): wherein the variables of Formula (I) are defined herein. This disclosure also provides pharmaceutical compositions comprising the compounds, uses of the compounds, and compositions for treatment of, for example, a metabolic or cardiovascular disorder. Further, the disclosure provides intermediates useful in the synthesis of compounds of Formula (I).

  本公开提供了用于抑制Delta-5 Desaturase ("D5D")的化合物。这些化合物具有一般的化学式（I）：其中化学式（I）中的变量在此处定义。本公开还提供了包括这些化合物的药物组合物，这些化合物的用途，以及用于治疗代谢或心血管疾病等疾病的组合物。此外，本公开提供了在合成化学式（I）化合物中有用的中间体。
• New Base Pairing Motifs. The Synthesis and Thermal Stability of Oligodeoxynucleotides Containing Imidazopyridopyrimidine Nucleosides with the Ability to Form Four Hydrogen Bonds
  作者：Noriaki Minakawa、Naoshi Kojima、Sadao Hikishima、Takashi Sasaki、Arihiro Kiyosue、Naoko Atsumi、Yoshihito Ueno、Akira Matsuda

  DOI：10.1021/ja0347686

  日期：2003.8.1

  The synthesis and thermal stability of oligodeoxynucleotides (ODNs) containing imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine nucleosides 1-4 (N(N), O(O), N(O), and O(N), respectively) with the aim of developing two sets of new base pairing motifs consisting of four hydrogen bonds (H-bonds) is described. The proposed four tricyclic nucleosides 1-4 were synthesized through the Stille coupling reaction of

  含有咪唑并[5',4':4,5]吡啶并[2,3-d]嘧啶核苷1-4 (N(N), O(O), N(O)的寡聚脱氧核苷酸 (ODN) 的合成和热稳定性) 和 O(N))，目的是开发两组由四个氢键（H 键）组成的新碱基配对基序。提出的四种三环核苷 1-4 是通过 5-碘咪唑核苷与合适的 5-甲锡烷基嘧啶衍生物的 Stille 偶联反应合成的，然后进行分子内环化。这些核苷被纳入 ODN 以研究 H 键合能力。当一个分子的三环核苷结合到每个 ODN（ODN I 和 II，每个 17mer）的中心时，没有观察到明显的碱基配对特异性，并且所有双链体都比含有天然 G:C 和 A:T 对的双链体更不稳定。另一方面，当三个三环核苷分子连续掺入每个 ODN（ODN III 和 IV，每个 17 聚体）的中心时，由于特定的碱基配对，观察到双链体的热和热力学稳定性。含有 N(O):O(N) 对的双链体的熔解温度 (T(m))
• 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