6-(3-氯丙基)氨基1,3-二甲基脲嘧啶 | 34654-81-4

• 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: 6-(3-氯丙基)氨基1,3-二甲基脲嘧啶
• 中文别名: 6-(3-氯丙基)氨基1,3-二甲基尿嘧啶；6-[(3-氯丙基)氨基]-1,3-二甲基尿嘧啶；6-((3-氯丙基)氨基)-1,3-二甲基尿嘧啶；1,3-二甲基-6-(γ-氯丙基氨基)-脲嘧啶；6-(3-氯丙基)氨基-1,3-二甲基尿嘧啶；6-[(3-氯丙基)氨基-1,3-二甲基尿嘧啶；6-(3-氯丙基)氨基1,3-二甲基脲嘧啶盐酸盐
• 英文名称: 6‑(3‑chloropropyl)amino‑1,3‑dimethyluracil
• 英文别名: 6-[(3-chloropropyl)amino]-1,3-dimethyluracil；6-(3-chloro-propylamino)-1,3-dimethyl-1H-pyrimidine-2,4-dione；6-(3-chloropropylamino)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione；6-(3-chloropropylamino)-1,3-dimethylpyrimidine-2,4-dione
• CAS: 34654-81-4
• 化学式: C₉H₁₄ClN₃O₂
• 分子量: 231.682
• InChiKey: RPYBDDBZRQGARJ-UHFFFAOYSA-N

物化性质

• 熔点：
  156.0 to 160.0 °C
• 沸点：
  342.9±52.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  室温下密封保存。

SDS

6-[(3-Chloropropyl)amino]-1,3-dimethyluracil
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 6-[(3-Chloropropyl)amino]-1,3-dimethyluracil

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 6-[(3-Chloropropyl)amino]-1,3-dimethyluracil
Percent: >98.0%(HPLC)(N)
CAS Number: 34654-81-4
Chemical Formula: C9H14ClN3O2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Slightly pale yellow
No data available
Odour:

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:159°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen chloride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-(3-氯丙基)氨基1,3-二甲基脲嘧啶 在 三正丙胺 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 、 乙酸乙酯 为溶剂， 生成 5-Cyanoethyl-1,3-dimethyl-6-[[3-[4-(2-ethoxyphenyl)-1-piperazinyl]propyl]amino]-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Uracil derivatives

  摘要：

  公式I中的化合物，在其中取代基和符号具有描述中指示的含义，是R5-HT.sub.1A激动剂和α1-肾上腺素受体阻滞剂。含有这些化合物作为活性成分的组合物对于治疗那些可以通过5-HT.sub.1A激动剂或α1-肾上腺素受体阻滞剂治疗的疾病是有用的。

  公开号：

  US06046329A1
• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 在 氯化亚砜 、 氯化铵 、 乙酸乙酯 作用下， 反应 6.5h， 生成 6-(3-氯丙基)氨基1,3-二甲基脲嘧啶
  参考文献：
  名称：

  一种乌拉地尔的制备方法

  摘要：

  本发明提供了一种乌拉地尔的制备方法。该制备方法包括：1,3‑二甲基‑6‑氨基脲嘧啶与3‑氨基‑1‑丙醇混合反应，制得6‑(3‑羟丙基氨基)‑1,3‑二甲基脲嘧啶；将6‑(3‑羟丙基氨基)‑1,3‑二甲基脲嘧啶和氯化亚砜混合反应，制得6‑(3‑氯丙基氨基)‑1,3‑二甲基脲嘧啶；将6‑(3‑氯丙基氨基)‑1,3‑二甲基脲嘧啶与1‑(2‑甲氧基苯基)哌嗪盐酸盐反应，得到乌拉地尔。本发明的制备方法的操作简单，试剂便宜易得，副反应少，收率高，并且得到的产品纯度好，有利于工业化生产。

  公开号：

  CN114057653A

文献信息

• Synthesis and structure–activity relationships of phenothiazine carboxylic acids having pyrimidine-dione as novel histamine H1 antagonists
  作者：Katsumi Kubota、Hirotaka Kurebayashi、Hirotaka Miyachi、Masanori Tobe、Masako Onishi、Yoshiaki Isobe

  DOI：10.1016/j.bmcl.2009.03.124

  日期：2009.5

  A series of phenothiazine carboxylic acid derivatives, having 6-amino-pyrimidine-2,4(1H,3H)-dione moiety via a appropriate linker, were synthesized and evaluated for their affinity toward human histamine H1 receptor and Caco-2 cell permeability. Selected compounds were further evaluated for their oral anti-histaminic activity in mice and bioavailability in rats. Finally, promising compounds were examined

  合成了一系列通过适当的接头具有6-氨基-嘧啶-2,4（1 H，3 H）-二酮部分的吩噻嗪羧酸衍生物，并评估了它们对人组胺H 1受体和Caco-2的亲和力细胞通透性。进一步评估了所选化合物在小鼠中的口服抗组胺活性和在大鼠中的生物利用度。最后，在小鼠OVA诱导的双相皮肤反应模型中检查了有希望的化合物的抗炎潜力。在所测试的化合物中，吩噻嗪乙酸化合物27在体内模型中均显示出组胺H 1受体拮抗活性和抗炎活性。
• 一种6-（3-氯丙基）氨基-1,3-二甲基脲嘧啶的制备方法
  申请人：沈阳信康药物研究有限公司

  公开号：CN113402469A

  公开（公告）日：2021-09-17

  本发明属于药物合成工艺技术领域，提供了一种6‑(3‑氯丙基)氨基‑1,3‑二甲基脲嘧啶的制备方法，以6‑(3‑羟丙基)氨基‑1,3‑二甲基脲嘧啶为原料，用氯化亚砜氯化得到6‑(3‑氯丙基)氨基‑1,3‑二甲基脲嘧啶。本反应直接以氯化亚砜为反应试剂和溶剂，收率可达85％以上，最高达到90％以上，纯度最高可达98％以上。相对于现有技术，不仅收率和纯度明显提高，而且后处理方便，后处理溶剂可以循环使用，更重要的是避免用到了可致癌且对人和环境有害的一类溶剂1,2‑二氯乙烷。在用于合成抗高血压药物乌拉地尔时，不仅减少了溶剂种类，且避免了药物质量分析中1,2‑二氯乙烷残留溶剂分析，是一种绿色、安全且非常适合工业化生产的制备方法。
• New and efficient technique for the synthesis of Urapidil using β-cyclodextrin as an inverse phase-transfer catalyst
  作者：Wen Li、Wenya Zhang、Xiaoqing Ma、Panpan Wang、Menghong Du

  DOI：10.1016/j.apcata.2012.01.030

  日期：2012.3

  procedure has been developed for the preparation of Urapidil, (6-(3-4-(2-methoxyphenyl) piperazin-1-yl] propyl} amino)-1,3-dimethyl pyrimidine-2,4-(1H, 3H)-dione), from 6-[(3-chloropropyl) amino]-1, 3-dimethyluracil and 1-(2-methoxyphenyl) piperazine hydrochloride under inverse phase-transfer catalysis (IPTC) conditions. To optimize the reaction conditions, the alkylation reaction was carried out with a

  已经开发了一种新颖而有效的方法来制备乌拉地尔（（6-（3-4-（2-甲氧基苯基）哌嗪-1-基]丙基}氨基）-1,3-二甲基嘧啶-2,4-在逆相转移催化（IPTC）条件下，由6-[（（3-氯丙基）氨基] -1、3-二甲基尿嘧啶和1-（2-甲氧基苯基）哌嗪盐酸盐制成（1H，3H）-二酮）。为了优化反应条件，用一系列反相转移催化剂，搅拌速度，反应时间，反应温度，摩尔比和催化剂负载量进行烷基化反应。此外，研究了影响反应速率的因素，得到的速率常数与拟一级反应速率方程式一致。当使用β-环糊精作为催化剂时，乌拉地尔为白色结晶粉末，分离率为82.6％，收率为99。
• 1,3-Disubstituierte Pyrrolidine
  申请人：BAYER AG

  公开号：EP0338331A1

  公开（公告）日：1989-10-25

  1,3-Disubstituierte Pyrrolidine können durch Umsetzung von entsprechenden und substituierten Pyrrolidinen mit Alkylderivaten hergestellt werden. Die 3-substituierten Pyrrolidine können als Wirkstoffe in Arzneimittel einge­setzt werden.

  1,3-二取代吡咯烷可以通过相应的和取代的吡咯烷与烷基衍生物反应制得。3-取代的吡咯烷可用作药物的活性成分。
• [DE] URACILDERIVATE<br/>[EN] URACIL DERIVATIVES<br/>[FR] DERIVES D'URACILE
  申请人：BYK GULDEN LOMBERG CHEMISCHE FABRIK GMBH

  公开号：WO1996017831A1

  公开（公告）日：1996-06-13

  (DE) Verbindungen der Formel (I), worin die Substituenten und Symbole die in der Beschreibung genannten Bedeutungen haben, stellen neue 5-HT1A-Agonisten und $g(a)1-Adrenozeptorenblocker dar.(EN) Disclosed are compounds of formula I, in which the substituents and symbols have the meanings indicated in the description. These compounds are novel 5-HT1A-agonists and $g(a)1-adrenoceptor blockers.(FR) L'invention concerne des composés de formule (I), où les substituants et les symboles ont la définition donnée dans la description. Ces composés constituent de nouveaux agonistes 5-HT1A et inhibiteurs d'adrénorécepteurs $g(a)1.

  本 invention 涉及化学式为(I)的化合物，其中取代基和符号根据描述具有特定含义。这种化合物是新型的5-HT1A激动剂和$g(a)1羟色胺受体阻滞剂。