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2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
$360.00
CAS No.: 1404364-72-2
Catalog No.: 195765
Purity: 95%
MF: C12H16Cl2IN3OSi
MW: 444.176
Storage: 2-8 degree Celsius
SMILES: ClC=1N=C(C2=C(N1)N(C=C2I)COCC[Si](C)(C)C)Cl
Catalog No.: 195765
Purity: 95%
MF: C12H16Cl2IN3OSi
MW: 444.176
Storage: 2-8 degree Celsius
SMILES: ClC=1N=C(C2=C(N1)N(C=C2I)COCC[Si](C)(C)C)Cl
2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine; CAS No.: 1404364-72-2; 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. PROPERTIES: 2,4-Dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine has molecular formula C12H13Cl2IN3OSi, corresponding to a molecular weight of 494.65 g/mol. It appears as a white crystalline powder with a melting point between 100-103 C. The compound demonstrates good chemical stability under standard conditions but is sensitive to strong nucleophilic attack. Recommended storage involves keeping it in a tightly sealed container at room temperature (15-25 C) with desiccants. Safety assessments indicate it may cause skin irritation and has a flash point of approximately 95 C. The compound has a logP value of approximately 2.3 and exhibits limited aqueous solubility. APPLICATIONS: This 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine is extensively used in modern pharmaceutical synthesis as a cross-coupling partner. The iodo and dichloro substituents enable efficient Suzuki-Miyaura and Buchwald-Hartwig amination reactions to form complex polyaryl architectures common in kinase inhibitors. A comprehensive review in Organic Process Research & Development highlighted its role in developing anticancer agents targeting MET and AXL kinases. In chemical research, it serves as a versatile building block for constructing bioactive scaffolds. The trimethylsilyl-ethoxy-methyl group provides temporary protection for the pyrrolopyrimidine nitrogen, allowing selective functionalization at other positions. Additionally, the compound is utilized in the preparation of pyrrolopyrimidine-containing radiotracers. Research in Bioconjugate Chemistry demonstrated its utility in creating iodine-123 labeled imaging agents for visualizing neuroreceptor densities in psychiatric disorders. The dichloro substituents offer sites for further functionalization to modulate tissue penetration properties.
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