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Replacement of aromatic fluorine by a methoxy group during reaction with methyl iodide in N , N ‐dimethylformamide solvent
Author(s) -
Chou TzunYu,
Vouros Paul,
David Mordechai,
Saha Manasi,
Giese Roger W.
Publication year - 1987
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200140107
Subject(s) - chemistry , methyl iodide , dimethylformamide , solvent , acetonitrile , derivative (finance) , iodide , medicinal chemistry , fluorine , chloride , uracil , methyl group , inorganic chemistry , organic chemistry , dna , group (periodic table) , biochemistry , financial economics , economics
The DNA base uracil was derivatized with pentafluorobenzoyl chloride, followed by methylation with methyl iodide in the presence of N , N ‐dimethylformamide (DMF). In addition to a 3‐pentafluoro‐benzoyl‐1 ‐methyl derivative of uracil, GC/MS analysis of the reaction mixture revealed the formation of an unusual product, whose molecular weight was 12 U higher than that of the prior derivative. This unexpected product has been identified as the 3‐( para ‐methoxytetrafluorobenzoyl)‐1‐methyl derivative of uracil. Isotopic labeling and related experiments have revealed that the DMF solvent contributes the oxygen atom of the methoxy group that replaces the para fluorine atom. This work allowed a single derivative to be obtained for the methylation reaction by changing the solvent to acetonitrile.