2-氨基-5,6-二甲基-4-羟基嘧啶 | 3977-23-9

• 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-5,6-二甲基-4-羟基嘧啶
• 中文别名: 5，6-二甲基-2-氨基-4-羟基嘧啶
• 英文名称: 2‐amino‐5,6‐dimethyl‐4‐hydroxypyrimidine
• 英文别名: 2-amino-5,6-dimethyl-4-hydroxypyrimidine；2-amino-5,6-dimethyl-3H-pyrimidin-4-one；2-amino-5,6-dimethyl-1H-pyrimidin-4-one；2-amino-5,6-dimethyl-4-pyrimidinol；2-Amino-4-hydroxy-5,6-dimethylpyrimidin
• CAS: 3977-23-9
• 化学式: C₆H₉N₃O
• mdl: MFCD00023258
• 分子量: 139.157
• InChiKey: APWRLAZEMYLHKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  333-337 °C(lit.)
• 沸点：
  341°C
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933599090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-Amino-5,6-dimethyl-4-hydroxypyrimidine
CAS-No. : 3977-23-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6H9N3O
Molecular Weight : 139,16 g/mol
Component Concentration
2-Amino-5,6-dimethyl-1H-pyrimidin-4-one
CAS-No. 3977-23-9 -
EC-No. 223-611-6

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 333 - 337 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2-氨基-5,6-二甲基-4-羟基嘧啶 在 三氯氧磷 作用下， 以86 %的产率得到4-氯-5,6-二甲基-嘧啶-2-胺
  参考文献：
  名称：

  胍基喹唑啉和嘧啶促进具有天然无义突变的细胞中提前终止密码子的通读

  摘要：

  使用小分子诱导提前终止密码子的通读是治疗由无义突变引起的遗传疾病和癌症的有前途的治疗方法，广泛使用 ataluren 治疗无义突变杜氏肌营养不良症就证明了这一点。在这里，我们描述了一系列新型胍基喹唑啉和嘧啶支架，它们在 HDQ-P1 乳腺癌细胞和mdx中诱导通读肌管。碱性叔胺与脂肪族疏水取代基与这些支架的末端胍氮的连接导致效力显着增加。通过在嘧啶环两侧添加疏水性取代基，在低至 120 nM 的浓度下诱导通读，并证明这些化合物与 ataluren 组合或作为独立治疗剂使用的潜力，进一步提高了效力。

  DOI：

  10.1016/j.bmcl.2022.128989
• 作为产物：
  描述：

  2-甲基-3-氧代丁酸甲酯 、 盐酸胍 在 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 生成 2-氨基-5,6-二甲基-4-羟基嘧啶
  参考文献：
  名称：

  Discovery and SAR of 6-Alkyl-2,4-diaminopyrimidines as Histamine H₄ Receptor Antagonists

  摘要：

  This report discloses the discovery and SAR of a series of 6-alkyl-2-aminopyrimidine derived histamine H4 antagonists that led to the development of JNJ 39758979, which has been studied in phase II clinical trials in asthma and atopic dermatitis. Building on our SAR studies of saturated derivatives from the indole carboxamide series, typified by JNJ 7777120, and incorporating knowledge from the tricyclic pyrimidines led us to the 6-alkyl-2,4-diaminopyrimidine series. A focused medicinal chemistry effort delivered several 6-alkyl-2,4-diaminopyrimidines that behaved as antagonists at both the human and rodent H4 receptor. Further optimization led to a panel of antagonists that were profiled in animal models of inflammatory disease. On the basis of the preclinical profile and efficacy in several animal models, JNJ 39758979 was selected as a clinical candidate; however, further development was halted during phase II because of the observation of drug-induced agranulocytosis (DIAG) in two subjects.

  DOI：

  10.1021/jm401727m

文献信息

• Combination of a serotonin receptor antagonist with a histidine decarboxylase inhibitor as a medicament
  申请人：Biofrontera Pharmaceuticals AG

  公开号：EP1321169A1

  公开（公告）日：2003-06-25

  The present invention relates to the use of (S)-α-fluoromethylhistidine and esters and pharmaceutically acceptable salts thereof in combination with a serotonin receptor antagonist or a pharmaceutically acceptable salt thereof as a medicament and for the manufacture of a medicament for treatment of a disease state which can be alleviated by treatment with a serotonin receptor antagonist and/or a histamine receptor antagonist.

  本发明涉及使用(S)-α-氟甲基组氨酸及其酯和药学上可接受的盐与5-羟色胺受体拮抗剂或其药学上可接受的盐结合作为药物，并用于制造一种治疗可通过使用5-羟色胺受体拮抗剂和/或组胺受体拮抗剂进行缓解的疾病状态的药物。
• Rho-kinase inhibitors
  申请人：BAYER CORPORATION

  公开号：US20040002508A1

  公开（公告）日：2004-01-01

  Disclosed are compounds and derivatives thereof, their synthesis, and their use as Rho-kinase inhibitors. These compounds are useful for inhibiting tumor growth, treating erectile dysfunction, and treating other indications mediated by Rho-kinase, e.g., coronary heart disease.

  本文披露了化合物及其衍生物、它们的合成以及它们作为Rho激酶抑制剂的用途。这些化合物可用于抑制肿瘤生长、治疗勃起功能障碍，以及治疗其他由Rho激酶介导的疾病，例如冠心病。
• PREPARATION METHOD FOR REVAPRAZAN HYDROCHLORIDE
  申请人：JIANGSU TASLY DIYI PHARMACEUTICAL CO., LTD.

  公开号：US20170267646A1

  公开（公告）日：2017-09-21

  Provided is a preparation method for revaprazan hydrochloride, the method comprising: (1) the preparation of 4-hydroxyl-2-(4-fluoroaniline)-5,6-dimethylpyrimidine; (2) the preparation of 4-chloro-2-(4-fluoroaniline)-5,6-dimethylpyrimidine; (3) the preparation of revaprazan hydrochloride. The method has advantages such as simple operations, high product purity, good yield and suitability for industrial production.

  提供了一种雷伐普兰盐酸盐的制备方法，该方法包括：（1）制备4-羟基-2-(4-氟苯胺)-5,6-二甲基嘧啶；（2）制备4-氯-2-(4-氟苯胺)-5,6-二甲基嘧啶；（3）制备雷伐普兰盐酸盐。该方法具有操作简单、产品纯度高、产率好且适合工业生产等优点。
• PROCESS FOR THE PREPARATION OF PTERIDINE DERIVATIVES
  申请人：Attolino Emanuele

  公开号：US20130090474A1

  公开（公告）日：2013-04-11

  The application discloses a process for the preparation of 5-deoxy-L-arabinose of formula (VI); comprising the conversion of a compound of formula (XII); wherein n is 0, 1 or 2; which can be used as intermediate for the synthesis of sapropterin.

  该申请披露了一种制备式（VI）的5-去氧-L-阿拉伯糖的过程；包括将式（XII）的化合物转化为中间体，其中n为0、1或2；该中间体可用于合成沙普替林。
• [EN] NEW EQUATORIALLY MODIFIED POLYMER LINKED MULTIMERS OF GUANOSINE-3', 5'-CYCLIC MONOPHOSPHATES<br/>[FR] NOUVEAUX MULTIMÈRES LIES A UN POLYMÈRE MODIFIÉ ÉQUATORIELLEMENT DES MONOPHOSPHATES DE GUANOSINE-3', 5'-CYCLIQUE
  申请人：BIOLOG LIFE SCIENCE INST FORSCHUNGSLABOR UND BIOCHEMICA-VERTRIEB GMBH

  公开号：WO2018010965A1

  公开（公告）日：2018-01-18

  Embodiments of the invention are directed to new equatorially modified polymer linked multimers of guanosine-3', 5'-cyclic monophosphate (cGMP) analogues that inhibit the cGMP-signaling system. The invention is also directed to related monomeric compounds, which may serve as monomeric precursors of the multimers, and/or also show itself inhibitory activity and/or impact the inhibitory activity of the related multimers. The invention further relates to the use of such compounds as reagents for signal transduction research and as modulators of cyclic nucleotide-regulated binding proteins and isoenzymes thereof, and as ligands for affinity chromatography, for antibody production or for diagnostic applications, e.g., on chip surfaces.

  本发明的实施例涉及新的赤道修饰聚合物连接的鸟苷-3'，5'-环磷酸鸟苷（cGMP）类似物的多聚体，其抑制cGMP信号传导系统。本发明还涉及相关的单体化合物，可以作为多聚体的单体前体，并且也显示出抑制活性和/或影响相关多聚体的抑制活性。本发明进一步涉及将这些化合物用作信号转导研究的试剂和循环核苷酸调节结合蛋白及其同功酶的调节剂，以及用作亲和层析的配体，用于抗体生产或用于诊断应用，例如在芯片表面。

表征谱图