2-氨基-4-氯吡咯并[2,3-d]嘧啶 | 84955-31-7

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷中间体
• 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: 2-氨基-4-氯吡咯并[2,3-d]嘧啶
• 中文别名: 2-氨基-4-氯吡咯并嘧啶；2-氨基-4-氯吡咯并[2,3-D]嘧啶；6-氯-7-脱氮鸟嘌呤
• 英文名称: 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine
• 英文别名: 2-amino-4-chloro-7H-pyrrolo[2,3-d ]pyrimidine；2-amino-4-chloropyrrolo[2,3-d]pyrimidine；2-amino-6-chloro-7-deazapurine；6-chloro-7-deazaguanine；2-amino-4-chloro-1H-pyrrolo[2,3-d]pyrimidine；4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine
• CAS: 84955-31-7
• 化学式: C₆H₅ClN₄
• mdl: MFCD07369229
• 分子量: 168.585
• InChiKey: VIVLSUIQHWGALQ-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217°C
• 沸点：
  346.6±52.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H319
• 储存条件：
  -20°C 冰箱

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and 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

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine
CAS number: 84955-31-7

---

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

---

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.

---

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.

---

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.

---

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.

---

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: C6H5ClN4
Molecular weight: 168.6

---

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, hydrogen chloride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

2-氨基-4-氯吡咯并[2,3-D]嘧啶是医药和化工制备中的常用中间体。吡咯[2,3-d]嘧啶化合物是一种重要的药物中间体，不仅在止痛和抗癌方面具有独特疗效，还能治疗风湿性关节炎、牛皮癣、糖尿病等疑难杂症。因此，这类化合物的应用前景广泛，近年来备受关注。

制备

目前合成吡咯[2,3-d]嘧啶化合物的方法主要有以下三种：以嘧啶化合物为底物构建吡咯环、以吡咯为母体构建嘧啶环和同时构建两种杂环。2-氨基-4-氯吡咯并[2,3-D]嘧啶的合成起始于2,6-二氨基-6-羟基嘧啶，经过关环、还原、氯代等步骤制备而成。其合成路线图如下：


反应信息

• 作为反应物：
  描述：

  2-氨基-4-氯吡咯并[2,3-d]嘧啶 在 copper(l) iodide 、 N,O-双三甲硅基乙酰胺 、 10% Pd/C 、 potassium carbonate 、 三苯基膦 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.67h， 生成 4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-yn-1-ol
  参考文献：
  名称：

  EC144 Is a Potent Inhibitor of the Heat Shock Protein 90

  摘要：

  Alkyne 40, 5-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylpent-4-yn-2-ol (EC144), is a second generation inhibitor of heat shock protein 90 (Hsp90) and is substantially more potent in vitro and in vivo than the first generation inhibitor 14 (BIIB021) that completed phase II clinical trials. Alkyne 40 is more potent than 14 in an Hsp90 alpha binding assay (IC50 = 1.1 vs 5.1 nM) as well as in its ability to degrade Her-2 in MCF-7 cells (EC50 = 14 vs 38 nM). In a mouse model of gastric tumors (N87), 40 stops tumor growth at 5 mg/kg and causes partial tumor regressions at 10 mg/kg (po, qdx5). Under the same conditions, 14 stops tumor growth only at 120 mg/kg, and does not induce partial regressions. Thus, alkyne 40 is approximately 20-fold more efficacious than 14 in mice.

  DOI：