2,4-二甲氧基-7h-吡咯并[2,3-d]嘧啶 | 90057-09-3

• 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: 2,4-二甲氧基-7h-吡咯并[2,3-d]嘧啶
• 英文名称: 2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidine
• 英文别名: 2,4-Dimethoxy-7H-pyrrolo<2,3-d>pyrimidin；2,4-dimethoxypyrrolo<2,3-d>pyrimidine；2,6-dimethoxypyrrolo<2,3-d>pyrimidine；2,4-dimethoxy-1H-pyrrolo[2,3-d]pyrimidine
• CAS: 90057-09-3
• 化学式: C₈H₉N₃O₂
• mdl: MFCD03425551
• 分子量: 179.178
• InChiKey: UBLQRBYFVAHEJK-UHFFFAOYSA-N

物化性质

• 熔点：
  216-217°C
• 沸点：
  321.5±52.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,4-Dimethoxypyrrolo[2,3-d]pyrimidine
Synonyms: 2,6-Dimethoxy-7-deazapurine

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

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Section 3. Composition/information on ingredients.
Ingredient name: 2,4-Dimethoxypyrrolo[2,3-d]pyrimidine
CAS number: 90057-09-3

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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.

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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.

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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.

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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.
Store in closed vessels, refrigerated.
Storage:

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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.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H9N3O2
Molecular weight: 179.2

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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.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,4-二甲氧基-7h-吡咯并[2,3-d]嘧啶 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,4-二羟基吡咯[2,3-d]嘧啶
  参考文献：
  名称：

  ara -7-deazaxanthosine-具有稳定N-糖基键的黄嘌呤核苷

  摘要：

  ARA -7- deazaxanthosine（2）的制备是通过相转移糖基化的2,4-二甲氧基- 7 ħ吡咯并[2,3- d ]嘧啶（图5b与halogenose）6。用三氯化硼除去优选在糖基化反应中形成的β-端基异构体8的苄基保护基，并用酸分离出2，4-二甲氧基。与黄嘌呤（1a）相反，7-脱氮嘌呤核苷2具有在酸水解时稳定的N-糖基键。通过比较嘌呤核苷与2的动力学参数描述了质子催化水解的反应机理，也解释了吡咯并[2,3- d ]嘧啶核苷2的稳定性。

  DOI：

  10.1002/jlac.198419840210
• 作为产物：
  描述：

  2-氨基-4-氯吡咯并[2,3-d]嘧啶 在 盐酸 、 copper(l) chloride 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 168.5h， 生成 2,4-二甲氧基-7h-吡咯并[2,3-d]嘧啶
  参考文献：
  名称：

  Seela, Frank; Driller, Hansjuergen; Liman, Ulrich, Liebigs Annalen der Chemie, 1985, p. 312 - 320

  摘要：

  DOI：

文献信息

• Condensed Heteroaromatic Ring Systems. XXI. Synthesis of Pyrrolo(2,3-d)pyrimidines and Pyrrolo(3,2-d)pyrimidines.
  作者：Takao SAKAMOTO、Chisato SATOH、Yoshinori KONDO、Hiroshi YAMANAKA

  DOI：10.1248/cpb.41.81

  日期：——

  Pyrrolo[2, 3-d]pyrimidines and pyrrolo[3, 2-d]pyrimidines were synthesized in high yields by the palladiumcatalyzed reaction of 4-acetylamino-5-bromopyrimidines and 5-acetylamino-4-iodopyrimidines with (Z)-1-ethoxy-2-(tributylstannyl)ethene followed by cyclization under acidic conditions.

  在钯催化下，4-乙酰氨基-5-溴嘧啶和 5-乙酰氨基-4-碘嘧啶与(Z)-1-乙氧基-2-(三丁基锡)乙烯反应，然后在酸性条件下环化，高产率合成了吡咯并[2,3-d]嘧啶和吡咯并[3,2-d]嘧啶。
• Condensed heteroaromatic ring systems. Part 24. Synthesis of rigidin, a pyrrolo[2,3-d]pyrimidine marine alkaloid
  作者：Takao Sakamoto、Yoshinori Kondo、Shuichiroh Sato、Hiroshi Yamanaka

  DOI：10.1039/p19960000459

  日期：——

  synthesized from 2,4-dimethoxy-7-phenylsulfonylpyrrolo[2,3-d]pyrimidine. Lithiation of the pyrrolo[2,3-d]pyrimidine followed by electrophilic substitution with N, 4-dimethoxy-N-methylbenzamide afforded a 6-(4-methoxy)benzoyl derivative which by alkaline hydrolysis and subsequent iodination was converted into 2,4-dimethoxy-5-iodopyrrolo [2,3-d] pyrimidin-6-yl 4-methoxyphenyl ketone. The palladium-catalysed

  海洋生物碱刚性蛋白是由2，4-二甲氧基-7-苯基磺酰基吡咯并[2，3- d ]嘧啶合成的。吡咯并[2,3- d ]嘧啶的锂化，然后用N，4-二甲氧基-N-甲基苯甲酰胺进行亲电取代，得到6-（4-甲氧基）苯甲酰基衍生物，其通过碱水解和随后的碘化反应转化为2,4 -二甲氧基-5-碘吡咯并[2，3- d ]嘧啶-6-基4-甲氧基苯基酮。用2-（4-甲氧基苯基）-1,3,2-二氧杂硼烷进行钯催化的芳基化反应，然后用三溴化硼脱甲基，得到刚性蛋白。
• Cyclisation of 7-Deazaxanthine-9-propionic Acid to an Active-Site-Directed, Irreversibly Acting Inhibitor of Xanthine Oxidase
  作者：Helmut Rosemeyer、Uwe Kretschmer、Frank Seela

  DOI：10.1002/hlca.19850680811

  日期：1985.12.18

  carbodiimide resulted in an intramolecular acylation at N(3) with formation of the tricyclic compound 5. Compound 5 - bearing a reactive lactam ring - is an active-site-directed, irreversibly acting inhibitor of xanthine oxidase from cow's milk.

  用3-溴丙酸乙酯对2,4-二甲氧基-7 H-吡咯并[2,3- d ]嘧啶（2）进行相转移烷基化，从而选择性地将乙基2-3-3-二甲氧基-7 H-吡咯并[2,3-] d ]嘧啶-7-丙酸酯（3a）。皂化和醚裂解后，获得官能化的7-脱氮黄嘌呤4b。的反应4B用H 2 O形水溶性碳化二亚胺导致在N（3）与地层三环化合物的分子内酰化5。化合物5 -带有反应性内酰胺环-是活性定点的，不可逆地作用于牛奶中的黄嘌呤氧化酶抑制剂。
• Total synthesis of a marine alkaloid, rigidin
  作者：Takao Sakamoto、Yoshinori Kondo、Shuichiroh Sato、Hiroshi Yamanaka

  DOI：10.1016/s0040-4039(00)76660-3

  日期：1994.5

  Rigidin, a marine alkaloid, was synthesized by the combination of acylation via lithiation and arylation by palladium-catalyzed reaction starting from 2,4-dimethoxypyrrolo[2,3-d]pyrimidine.
• ROSEMEYER, HELMUT;KAISER, KLAUS;KRETSCHMER, UWE;SEELA, FRANK, BIO-ORG. HETEROCYSLES, 1986: SYNTH., METH. AND BIOACTIV.: PROC. 4TH FECHE+
  作者：ROSEMEYER, HELMUT、KAISER, KLAUS、KRETSCHMER, UWE、SEELA, FRANK

  DOI：——

  日期：——