5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶 | 22276-95-5

• 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 - 吡咯并嘧啶类
• 中文名称: 5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶
• 中文别名: 5-溴-4-氯-7H-吡咯[2,3-D]嘧啶；7-溴-6-氯-7-脱氮杂嘌呤；5-溴-4-氯-7H-吡咯并[2.3-d]嘧啶
• 英文名称: 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 7-bromo-6-chloro-7-deazapurine；5-bromo-4-chloropyrrolo[2,3-d]pyrimidine；4-chloro-5-bromopyrrolo[2,3-d]pyrimidine
• CAS: 22276-95-5
• 化学式: C₆H₃BrClN₃
• mdl: MFCD09702029
• 分子量: 232.467
• InChiKey: OXLMTRZWMHIZBY-UHFFFAOYSA-N

物化性质

• 熔点：
  221-225℃
• 沸点：
  221.0±50.0 °C(Predicted)
• 密度：
  2.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险等级：
  6.1
• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3
• 危险品运输编号：
  UN 2811 6.1 / PGIII
• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P301+P310
• 危险性描述：
  H301
• 储存条件：
  室温

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 7-Bromo-6-chloro-7-deazapurine
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.
CAS-No. : 22276-95-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 3), H301
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
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)
H301 Toxic if swallowed.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
Synonyms : 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
Formula : C6H3BrClN3
Molecular Weight : 232,47 g/mol
CAS-No. : 22276-95-5
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
7-Bromo-6-chloro-7-deazapurine
Acute Tox. 3; H301 -
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
7-Bromo-6-chloro-7-deazapurine
Xn, R22 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

---

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. Take victim immediately to hospital. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
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

---

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), Hydrogen chloride gas, Hydrogen bromide gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. 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
Prevent further leakage or spillage if safe to do so. 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.

---

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.
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.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

---

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
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 N99 (US) or type P2 (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
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

---

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: 221 - 225 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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- log Pow: 1,946
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

---

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
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

---

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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

---

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.

---

SECTION 14: Transport information
UN number
ADR/RID: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (7-Bromo-6-chloro-7-deazapurine)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (7-Bromo-6-chloro-7-deazapurine)
IATA: Toxic solid, organic, n.o.s. (7-Bromo-6-chloro-7-deazapurine)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

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
For this product a chemical safety assessment was not carried out

---

SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H301 Toxic if swallowed.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
Further information
Copyright 2013 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.

制备方法与用途

用途

5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶是一种氮杂环化合物，主要用于医药化学中间体的合成。它可用于合成生物大分子和生物激素。

制备工艺

将18.69克（105.00毫摩尔）1-溴吡咯烷-2,5-二酮缓慢加入到4-氯-7H-吡咯并[2,3-d]嘧啶（10.75克）溶解在150毫升二氯甲烷中的悬浮液中。反应混合物在室温下搅拌过夜。

反应完成后，可以观察到大量的沉淀物形成。将反应体系静置一段时间后可观察到固液两相分层。过滤收集沉淀物，并在减压下除去滤液，再用二氯甲烷清洗固体即可得到目标产物5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶。

反应信息

• 作为反应物：
  描述：

  5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶 在 氨 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 18.5h， 生成 7-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  腺苷激酶抑制剂。1. 5-碘代结核菌素类似物的合成，酶抑制和抗癫痫活性。

  摘要：

  腺苷受体激动剂产生多种治疗上有用的药理学。然而，迄今为止，由于剂量限制的副作用，它们未能成功进行临床开发。腺苷激酶抑制剂（AKIs）代表了另一种策略，因为AKIs可以以更多位点和事件特异性的方式提高局部腺苷水平，从而以更大的治疗窗口引发所需的药理作用。从5-碘代小球蛋白（IC50 = 0.026 microM）和5'-氨基-5'-脱氧腺苷（IC50 = 0.17 microM）作为分离的人AK的主要抑制剂开始，各种吡咯并[2,3-d]嘧啶核苷类似物通过使用钠盐介导的糖基化方法将5-取代的4-取代的4-氯吡咯并[2,3-d]嘧啶碱基与核糖类似物偶联来设计和制备。5'-氨基-5' 发现5-溴和5-碘结核菌素的β-脱氧类似物是迄今为止报道的最有效的AKI（IC50S <0.001 microM）。在大鼠最大电击（MES）诱发的癫痫发作试验中，几种有效的AKIs表现出抗惊厥活性。

  DOI：

  10.1021/jm000024g
• 作为产物：
  描述：

  4-氯吡咯并嘧啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶
  参考文献：
  名称：

  某些4-和4,5-二取代的7-[（2-羟基乙氧基）甲基]吡咯并[2,3-d]嘧啶的合成及抗病毒活性。

  摘要：

  一系列先前制备的结核菌素类似物的体外评估表明，某些5-卤素取代的类似物对人巨细胞病毒（HCMV）的活性浓度低于在未感染细胞中产生可比细胞毒性的浓度。相反，结核菌素在所有抗病毒浓度下均具有细胞毒性。即使5-取代的化合物的抗病毒选择性很小，这一观察结果也使我们制备了一系列无环类似物。用（2-乙酰氧基乙氧基）甲基溴（2a）处理4-氯吡咯并[2,3-d]嘧啶（2）的钠盐，得到无环核苷4-氯-7-[（2-乙酰氧基乙氧基）甲基]吡咯[2，3-d]嘧啶（3）。用甲醇盐，甲胺和二甲胺对4-氯基进行亲核取代，得到相应的4-取代的化合物4、5和6 分别以良好的产量。用二氯甲烷中的N-氯代琥珀酰亚胺，N-溴代琥珀酰亚胺和一氯化碘分别在化合物3的C-5位进行亲电子取代（氯化，溴化和碘化）。在室温下用甲醇氨从这些中间体（7a-9a）除去乙酰基，得到4-氯-7-的5-氯（7b），5-溴（8b）和5-碘（9b）衍生物。

  DOI：

  10.1021/jm00119a006

文献信息

• [EN] PYRROLOTRIAZINONE DERIVATIVES AS PI3K INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLOTRIAZINONE EN TANT QU'INHIBITEURS DES PI3K
  申请人：ALMIRALL SA

  公开号：WO2014060432A1

  公开（公告）日：2014-04-24

  New pyrrolotriazinone derivatives having the chemical structure of formula (I), are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks)

  新的吡咯三唑酮衍生物具有化学结构式（I），公开；以及它们的制备方法，包括它们的药物组合物和它们作为磷脂酰肌醇3-激酶（PI3Ks）抑制剂在治疗中的应用。
• IRAK DEGRADERS AND USES THEREOF
  申请人：Kymera Therapeutics, Inc.

  公开号：US20190192668A1

  公开（公告）日：2019-06-27

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。
• [EN] PYRROLOPYRIMIDINES<br/>[FR] PYRROLOPYRIMIDINES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2009016132A1

  公开（公告）日：2009-02-05

  The present invention relates to compounds or pharmaceutically-acceptable salts thereof, processes for preparing them, pharmaceutical compositions containing them and their use in therapy. The invention particularly relates to compounds that are polo-like kinase (PLKs) inhibitors useful for the treatment of disease states mediated by PLK, especially PLK4, in particular such compounds that are useful in the treatment of pathological processes which involve an aberrant cellular proliferation, such as tumour growth, rheumatoid arthritis, restenosis and atherosclerosis.

  本发明涉及化合物或其药用盐，制备它们的方法，含有它们的药物组合物以及它们在治疗中的用途。该发明特别涉及一类极化样激酶（PLKs）抑制剂化合物，用于治疗由PLK介导的疾病状态，特别是PLK4，特别是在治疗涉及异常细胞增殖的病理过程中有用的化合物，如肿瘤生长、类风湿性关节炎、再狭窄和动脉粥样硬化。
• [EN] PROTEIN KINASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINES KINASES
  申请人：PHARMASCIENCE INC

  公开号：WO2015077866A1

  公开（公告）日：2015-06-04

  The present invention relates to a novel family of protein kinase inhibitors, more specifically the present invention is directed to inhibitors of the members of the Tec or Src protein kinase families. The present invention also relates to processes for the preparation of these compounds, to the pharmaceutical composition comprising them, and to their use in the treatment of proliferative, inflammatory, infectious or autoimmune diseases, disorder or condition in which protein kinase activity is implicated. More particularly, the present invention relates to a compound of Formula I.

  本发明涉及一种新型蛋白激酶抑制剂家族，更具体地说，本发明是针对Tec或Src蛋白激酶家族成员的抑制剂。本发明还涉及制备这些化合物的方法，包括含有它们的药物组合物，以及它们在治疗蛋白激酶活性参与的增殖性、炎症性、感染性或自身免疫疾病、紊乱或病症中的用途。更具体地说，本发明涉及一种I式化合物。
• [EN] ERBB INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE ERBB ET LEURS UTILISATIONS
  申请人：UNIV CALIFORNIA

  公开号：WO2017184775A1

  公开（公告）日：2017-10-26

  Described herein, inter alia, are compositions of ErbB modulators and methods of using the same.

  本文描述了ErbB调节剂的组成和使用方法。