2-氨基-5-甲基-4-嘧啶醇 | 15981-91-6

• 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-氨基-5-甲基-4-嘧啶醇
• 英文名称: 5-methylisocytosine
• 英文别名: 2-amino-5-methyl-1H-pyrimidin-6-one
• CAS: 15981-91-6
• 化学式: C₅H₇N₃O
• 分子量: 125.13
• InChiKey: YKUFMYSNUQLIQS-UHFFFAOYSA-N

物化性质

• 熔点：
  277-279 °C
• 密度：
  1.44±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S39
• 危险类别码：
  R41
• WGK Germany：
  1
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Amino-5-Methyl-4-Pyrimidinol
: CBR00408
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Serious eye damage (Category 1), H318
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
R41
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
Harmful if swallowed.
Causes serious eye damage.
Precautionary statement(s)
Wear protective gloves/ eye protection/ face protection.
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
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 125,13 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Amino-5-Methyl-4-Pyrimidinol
Acute Tox. 4; Eye Dam. 1; <= 100 %
H302, H318
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Amino-5-Methyl-4-Pyrimidinol
Xn, R22R41 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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 vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
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.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
Face shield and safety glasses 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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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 No data available
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) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
No data available
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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. 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
Further information
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

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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-甲基-4-嘧啶醇 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 8.0h， 以80%的产率得到胸腺嘧啶
  参考文献：
  名称：

  新的嘧啶和嘧啶并[1,2- a ]嘧啶衍生物。基于胍的胸腺嘧啶合成的副产物

  摘要：

  报道了三个以前未知的杂环的分离，结构阐明，定向制备和一些衍生物。由于基于胍的胸腺嘧啶的合成，这些新颖的化合物分别显示出取代的和稠合的嘧啶结构。

  DOI：

  10.1002/jhet.5570280205
• 作为产物：
  描述：

  2'-脱氧-5-甲基异胞苷 在 盐酸 作用下， 以 水 为溶剂， 生成 2-氨基-5-甲基-4-嘧啶醇
  参考文献：
  名称：

  含有5-甲基异胞嘧啶-鸟嘌呤和异鸟嘌呤-胞嘧啶碱基对的平行链寡核苷酸双链体

  摘要：

  制备包含5-甲基异胞嘧啶-鸟嘌呤和/或异鸟嘌呤-胞嘧啶碱基对的平行链寡核苷酸。当2'-脱氧-5-甲基异胞苷（2a）和2'-脱氧异鸟苷（3）的亚磷酰胺用于固相合成时，偶联效率高于99％。在am衍生物4a，b的情况下，2'-脱氧-5-甲基异胞苷（1a）的糖基键对酸稳定。长时间暴露于氨中会发生脱嘧啶作用。使用the准分子荧光明确确定了平行链（ps）双链体的取向。反平行（aps）双链体d（A 12）•d（T 12）（25•26当两个中心的腺嘌呤-胸腺嘧啶碱基对被异鸟嘌呤-胞嘧啶对取代时，变为平行方向。发现包含5-甲基异胞嘧啶-鸟嘌呤碱基对的ps-双链体的热稳定性显着低于具有异鸟嘌呤-胞嘧啶对的ps-双链体的热稳定性。根据CD光谱，与aps对应物相比，ps-DNA-DNA或DNA-RNA杂种在二级结构上表现出差异。

  DOI：

  10.1016/s0040-4020(99)00511-6

文献信息

• [EN] HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS<br/>[FR] COMPOSÉS HÉTÉROAROMATIQUES ET LEUR UTILISATION COMME LIGANDS DE LA DOPAMINE D1
  申请人：PFIZER

  公开号：WO2014072881A1

  公开（公告）日：2014-05-15

  The present invention provides, in part, compounds of Formula I: and pharmaceutically acceptable salts thereof and N-oxides thereof; processes and intermediates for preparation of; and compositions and uses thereof. The present invention further provides D1 agonists with reduced D1R desensitization, D1 agonists with a reduced β- arrestin recruitment activity relative to Dopamine, D1 agonists interacting significantly with the Ser188 but not significantly with the Ser202 of a D1R when binding to the D1R, D1 agonists interacting less strongly with the Asp103 and interacting less strongly with the Ser198 of a D1R when binding to the D1R, and their uses.

  本发明部分提供了化合物I的公式：及其药学上可接受的盐和N-氧化物；制备的过程和中间体；以及其组合物和用途。本发明进一步提供了具有减少D1R耐受性的D1激动剂，相对于多巴胺具有减少β-阿雷斯汀招募活性的D1激动剂，当结合到D1R时与D1R的Ser188显著相互作用但与Ser202的相互作用不显著的D1激动剂，当结合到D1R时与D1R的Asp103相互作用较弱并且与Ser198相互作用较弱的D1激动剂，以及它们的用途。
• HETEROARYL DERIVATIVES AS CFTR MODULATORS
  申请人：Ruah Sara Hadida

  公开号：US20090221597A1

  公开（公告）日：2009-09-03

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”), compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及调节ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节蛋白（“CFTR”），以及相关的组合物和方法。本发明还涉及使用这些调节剂治疗ABC转运蛋白介导的疾病的方法。
• TET‐Like Oxidation in 5‐Methylcytosine and Derivatives: A Computational and Experimental Study
  作者：Niko S. W. Jonasson、Rachel Janßen、Annika Menke、Fabian L. Zott、Hendrik Zipse、Lena J. Daumann

  DOI：10.1002/cbic.202100420

  日期：2021.12.2

  The reactivity of a biomimetic iron(IV)-oxo complex 1 towards a number of methylated cytosine and uracil substrates was investigated. The reaction rates are in very good agreement with the calculated BDEs. C-Methylated compounds such as 5mC, T and 5miC possess a different reactivity than the solely N-methylated compounds 1mC and 1mU.

  研究了仿生铁 (IV)-氧复合物1对多种甲基化胞嘧啶和尿嘧啶底物的反应性。反应速率与计算的 BDE 非常吻合。 C-甲基化化合物如 5mC、T 和 5m i C 具有与单独的N-甲基化化合物 1mC 和 1mU 不同的反应性。
• The 5-Methylisocytosineβ-D-Ribopyranosyl (4′ → 2′)-Oligonucleotide
  作者：Jan W. Bats、Christian Miculka

  DOI：10.1002/hlca.200690024

  日期：2006.2

  had led to the expectation that a 5-methylisocytosine β-D-ribopyranosyl (= D-pr(MeisoC)) based (4′  2′)-oligonucleotide would pair inter alia with D-pr(isoG) and L-pr(G) based oligonucleotides (D-pr and L-pr = pyranose form of D- and L-ribose, resp.). Remarkably, we could not observe pairing with the D-pr(isoG) oligonucleotide but only with the L-pr(G) oligonucleotide. Our interpretation concludes

  在Eschenmoser对吡喃糖基RNA（'p-RNA'）的研究中，我们研究了5-甲基异胞苷衍生物的合成和碱基配对特性。先前确定的p-RNA碱基配对模式的明确限制导致人们期望基于5-甲基异胞嘧啶β -D-核糖吡喃糖基（= D-pr（Me isoC））的（4'2'）-寡核苷酸将配对特别带有基于D-pr（isoG）和L-pr（G）的寡核苷酸（D-pr和L-pr = D-和L-核糖的吡喃糖形式，分别）。值得注意的是，我们无法观察到与D-pr（isoG）寡核苷酸配对，而只能观察到与L-pr（G）寡核苷酸配对。我们的解释认为，这一发现（乍看之下令人惊讶）是由isoC特有的核苷扭转角的变化引起的。
• Pyrimidine to pyrimidine transformation process
  申请人：Research Corporation

  公开号：US04171429A1

  公开（公告）日：1979-10-16

  There is provided a novel process for pyrimidine to pyrimidine transformations by the displacement of the 1,2,3-portion of a pyrimidine by a 1,3-ambident nucleophile. The novel process requires that the 1 and 3 nitrogens of the pyrimidine moiety be substituted. The novel process makes available, inter alia, novel uracils, simple methods of radioisotopically labeling pyrimidine nuclei, a simple and inexpensive method of preparing the important antiviral and antileukemic material pseudoisocytidine and its new active analog 2'-deoxypseudoisocytidine.

  提供了一种新的嘧啶转化为嘧啶的方法，通过1,3-双亲核烷基在嘧啶的1,2,3-部分的取代来实现。这种新方法要求嘧啶基团的1和3氮原子被取代。该新方法提供了新的尿嘧啶，放射性同位素标记嘧啶核的简单方法，以及制备重要的抗病毒和抗白血病材料伪异胞嘧啶及其新的活性类似物2'-去氧伪异胞嘧啶的简单且廉价方法。