KILO-SCALE SYNTHESIS PROCESS FOR 2′-O-(2-METHOXYETHYL)-PYRIMIDINE DERIVATIVES
| Autor: | Bruce S. Ross, Mingming Han, Quanlai Song |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Boron Compounds
Pyrimidine Base (chemistry) Pyridines Chemistry Pharmaceutical chemistry.chemical_element Cytidine Biochemistry law.invention chemistry.chemical_compound Hydrolysis law Genetics Organic chemistry Crystallization Boron Uridine chemistry.chemical_classification Chromatography Chemistry Esters General Medicine Extraction Purification Pyrimidines Models Chemical Scientific method Yield (chemistry) Molecular Medicine |
| Zdroj: | Nucleosides, Nucleotides & Nucleic Acids. 24:815-818 |
| ISSN: | 1532-2335 1525-7770 |
| Popis: | We describe an improved process to produce 2'-O-(2-methoxyethyl)-pyrimidines. Starting with commercially available O-2,2'-anhydro-5-methyluridine and tris-(2-methoxyethyl)borate, we modified the ring-opening reaction conditions and changed to a continuous extraction purification method to give 2'-O-(2-methaxyethyl)-5-methyluridine. The dimethoxytritylation 5'/3' ratios and yield were improved by the use of 2,6-lutidine as the base. Conditions to convert to the 5'-methylcytidine analog and its isolation by crystallization were optimized. Final benzoylation was improved by developing a method to selectively hydrolyze benzoyl ester impurities. |
| Databáze: | OpenAIRE |
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