4-氨基-2-甲氧基嘧啶 | 3289-47-2

• 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: 4-氨基-2-甲氧基嘧啶
• 中文别名: 2-甲氧基-4-二氨基嘧啶
• 英文名称: 4-amino-2-methoxypyrimidine
• 英文别名: 4-Amino-2-methoxy-pyrimidin；2-Methoxy-4-amino-pyrimidin；2-methoxy-4-aminopyrimidine；2-methoxypyrimidin-4-amine；2-methoxypyrimidine-4-amine；2-(methyloxy)-4-pyrimidinamine；2-Methoxy-pyrimidin-4-ylamine
• CAS: 3289-47-2
• 化学式: C₅H₇N₃O
• mdl: MFCD00128201
• 分子量: 125.13
• InChiKey: DHYLZDVDOQLEAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  294.4±32.0 °C(Predicted)
• 密度：
  1.224
• 溶解度：
  二甲基亚砜：60 mg/mL（479.50 mM）
• 物理描述：
  Solid

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

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36,R36/37/38,R22
• WGK Germany：
  3
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  应存于室温、避光且在惰性气体环境中。

SDS

Material Safety Data Sheet

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

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Amino-2-methoxypyrimidine
CAS number: 3289-47-2

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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, refrigerated.

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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

制备方法与用途

生物活性

2-O-甲基胞嘧啶是一种 O-烷基化类似物和 DNA 的加合物，属于受损的核碱基。

靶点

Human 内源性代谢物

体外研究

受损的核碱基可能会导致 DNA 突变，从而引发各种疾病，如癌症。

反应信息

• 作为反应物：
  描述：

  4-氨基-2-甲氧基嘧啶 在 盐酸 、 水 作用下， 反应 1.0h， 以91.2%的产率得到胞嘧啶
  参考文献：
  名称：

  合成胞嘧啶的工艺

  摘要：

  本发明公开了一种合成胞嘧啶的工艺，工艺如下：以3‑羟基丙烯腈化合物及O‑甲基异脲化合物或S‑甲基异硫脲化合物或S‑乙基异硫脲化合物或S‑苄基异硫脲化合物为原料；制备时，将催化剂及有机溶剂投入反应釜中搅拌后，再投入原料；升温到50～90℃反应8～12小时；蒸出溶剂，得到中间体；向中间体中加入浓盐酸，升温至70～100℃保温1～2小时；加入水进行热过滤，把得到的滤液冷却至室温；向滤液中滴加氢氧化钠溶液调节pH为7～7.5，冷却至10～15℃；冷却后过滤、水洗，烘干后即可得到胞嘧啶。优点是：本发明工艺步骤简单、生产周期短且成本低；而且本发明原料转化率高，合成的产品质量好、收率高，适合工业化生产。

  公开号：

  CN103896859B
• 作为产物：
  描述：

  4-氨基-2-氯嘧啶 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以50%的产率得到4-氨基-2-甲氧基嘧啶
  参考文献：
  名称：

  Peptide deformylase inhibitors

  摘要：

  本发明涉及一种化合物，其化学式为（I）：或其药用可接受的盐，相应的药物组合物，化合物制备和治疗方法，用于治疗细菌感染和抑制细菌肽变形酶（PDF）活性。

  公开号：

  US08901119B2

文献信息

• 吲哚类化合物及其制备方法、药物组合物和用途
  申请人：中国医学科学院药物研究所

  公开号：CN110483366B

  公开（公告）日：2022-09-16

  本发明公开了一类吲哚类化合物及其制备方法、药物组合物和用途，具体而言，本发明涉及通式I所示的吲哚类衍生物及其可药用盐，及其制备方法，含有一个或多个该类化合物的组合物，和该类化合物在制备、预防和/或治疗与IDO1和/或TDO相关的疾病药物中的用途。
• Co₂(CO)₈ as a Solid CO (g) Source for the Amino Carbonylation of (Hetero)aryl Halides with Highly Deactivated (Hetero)arylamines
  作者：Srinivas Cheruku、Ayyiliath M Sajith、Yatheesh Narayana、Poornima Shetty、Sandhya C Nagarakere、Kunigal S Sagar、Kumara N Manikyanally、Kanchugarkoppal Subbegowda Rangappa、Kempegowda Mantelingu

  DOI：10.1021/acs.joc.0c02999

  日期：2021.4.16

  Carbonylation of (hetero)aryl iodides/bromides with highly deactivated 2-aminopyridines using Pd–Co(CO)4 bimetallic catalysis is accomplished. The use of Co2(CO)8 as a solid CO(g) source enhanced reaction rates observed when compared to CO(g), and excellent yields highlight the versatility of the developed protocol. A wide range of electronically and sterically demanding heterocyclic amines and (hetero)aryl

  使用Pd–Co（CO）4双金属催化，可高度失活的2-氨基吡啶与（杂）芳基碘化物/溴化物进行羰基化反应。与CO（g）相比，使用Co 2（CO）8作为固体CO（g）源可提高反应速度，并且出色的收率突出了所开发方案的多功能性。用于本研究的各种电子和空间要求性的杂环胺和（杂）芳基碘化物/溴化物可产生优异的氨基羰基化产物收率。所开发的方法进一步扩展为合成锥虫布鲁西和荧光素酶抑制剂。
• Tyrosine kinase inhibitors
  申请人：——

  公开号：US20020137755A1

  公开（公告）日：2002-09-26

  The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, inflammatory diseases, and the like in mammals.

  本发明涉及抑制、调节和/或调控酪氨酸激酶信号传导的化合物，含有这些化合物的组合物，以及使用它们治疗依赖于酪氨酸激酶的疾病和病况的方法，如在哺乳动物中的血管生成、癌症、肿瘤生长、动脉粥样硬化、老年性黄斑变性、糖尿病视网膜病变、炎症性疾病等。
• Studies on Nucleosides and Nucleotides. VIII. Preparation and Reactions of Triphenylphosphoranediylnucleosides
  作者：Junji Kimura、Kentaro Yagi、Hideyuki Suzuki、Oyo Mitsunobu

  DOI：10.1246/bcsj.53.3670

  日期：1980.12

  The reaction of uridine, N4-benzoylcytidine, guanosine, and N6-p-toluoyladenosine with diethyl azodicarboxylate and triphenylphosphine resulted in the formation of the corresponding 2′,3′-O-(triphenylphosphoranediyl)-cyclonucleosides. On the other hand, adenosine afforded, under similar conditions, 3′,5′-O-(triphenylphosphoranediyl)adenosine (19). The difference can be explained in terms of the acidity

  尿苷、N4-苯甲酰胞苷、鸟苷和 N6-对甲苯酰腺苷与偶氮二羧酸二乙酯和三苯基膦的反应导致形成相应的 2',3'-O-（三苯基正膦二基）-环核苷。另一方面，在类似条件下，腺苷可提供 3',5'-O-（三苯基正膦二基）腺苷 (19)。这种差异可以用核苷碱基部分的酸度来解释。2',3'-O-(三苯基正膦二基)-O2,5'-环尿苷，N4-苯甲酰基-2',3'-O-(三苯基正膦二基)-O2,5'-环胞苷，2',3'的反应-O-(三苯基正膦二基)-N3,5'-环鸟苷或N6-p-toluoyl-2',3'-O-(三苯基正膦二基)-N3,5'-环腺苷与亲核试剂和亲电试剂添加相应的核苷衍生物游离的 2'-和 3'-羟基。因此 2', 3'-O-三苯基正膦二基作为保护基团，在反应产物的后处理过程中很容易去除。19与异氰酸苯酯反应制...
• [EN] OXADIAZOLYLTHIOPHENE DERIVATIVES USEFUL AS HISTONE DEACETYLASE INHIBITORS<br/>[FR] DÉRIVÉS D'OXADIAZOLYLTHIOPHÈNE À UTILISER EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE
  申请人：KARUS THERAPEUTICS LTD

  公开号：WO2019166824A1

  公开（公告）日：2019-09-06

  A compound of Formula I : (I) or a pharmaceutically acceptable salt thereof, wherein: each R' is QR1; each Q is independently selected from a bond, -C1-C10 alkylene, -C2-C10 alkenylene, -C(O)-, -C(O)O-, -C(O)N(R1)-, -C(O)N(R1)SO2- -N(R1)C(O)-, - N(R1)-, -N(SO2(R1)), -N(R1)SO2- -C(O)NR4R5-, -N(R4R5)C(O)-, -N(R4R5)- - S-, -SO-, -SO2-, -S(O)O-, -SO2N(R1)- and -O-; each R1 is independently selected from H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, C1-C10 heteroalkyl, aryl, heteroaryl, C3-C10 cycloalkyl, -(C1-C10 alkylene)-C3-C10 cycloalkyl, halogen, cyano, C1-C10 alkylene- aryl, C1-C10 alkylene heteroaryl, C1-C10 heterocycloalkyl and -(C1-C10 alkylene)- C1-C10 heterocycloalkyl. The compounds are inhibitors of HDAC and therefore have potential utility in the therapy of a number of conditions including cancer and inflammation.

  一种Formula I的化合物：(I)或其药学上可接受的盐，其中：每个R'是QR1；每个Q独立地选自键，-C1-C10烷基，-C2-C10烯基，-C(O)-，-C(O)O-，-C(O)N(R1)-，-C(O)N(R1)SO2-，-N(R1)C(O)-，-N(R1)-，-N(SO2(R1))，-N(R1)SO2-，-C(O)NR4R5-，-N(R4R5)C(O)-，-N(R4R5)-，-S-，-SO-，-SO2-，-S(O)O-，-SO2N(R1)-和-O-；每个R1独立地选自H，C1-C10烷基，C2-C10烯基，C2-C10炔基，C1-C10卤代烷基，C1-C10杂原子烷基，芳基，杂芳基，C3-C10环烷基，-(C1-C10烷基)-C3-C10环烷基，卤素，氰基，C1-C10烷基-芳基，C1-C10烷基-杂原子芳基，C1-C10杂环烷基和-(C1-C10烷基)-C1-C10杂环烷基。这些化合物是HDAC的抑制剂，因此在治疗包括癌症和炎症在内的多种疾病中具有潜在用途。