ELECTROCHEMICAL REDUCTION OF PYRIMIDINE, CYTOSINE AND RELATED COMPOUNDS: POLAROGRAPHY AND MACROSCALE ELECTROLYSIS. Report No. 63
The electrochemical reduction of pyrimidine and certain derivatives was investigated over the normal pH range by polarography, coulometry, and macroscale electrolysis. The reduction products were examined chemically, polarographically, and spectrophotometrically. Pyrimidine is first reduced at the 3,4 position in a le process to a free radical, which may dimerize or be reduced (le process) to 3,4-dihydropyrimidine; the latter can be further reduced (2e process) to tetrahydropyrimidine. The 2-amino- and 2-amino-4- methylpyrimidines are reduced in two le steps, first to a free radical and then to the 3,4-dihydro derivative. 4-Amino-2,6-dimethylpyrimidine gives a single 4e wave, which likeIy involves 2e reduction to the 3,4-dihydro compound followed by deamination to 2,6-dimethylpyrimi dine, which is reduced (2e prccess) to 2,6- dimethyl-3,4dihydropyrimidine. Cytosine (4-amino-2-hydroxypyrimidine) undergoes a 3e reduction, which involves 2e reduction of the 3,4 N = C bond, deamination to form 2-hydroxyPyrimidine and le reduction of the latter to a free radical which dimerizes. 2-Hydroxypyrimidine itself shows only le reduction. The dihydro and tetrahydro products are unstable in aqueous solution; pseudo first-order rate of disappearance is shown by the two compounds examined. In general, 4-amino- pyrimidines having the 3,4 position hydrogenated deaminate readily to generate the reducible 3,4 N = C bond. (auth)
- Research Organization:
- Michigan. Univ., Ann Arbor
- NSA Number:
- NSA-15-030531
- OSTI ID:
- 4840628
- Report Number(s):
- TID-13816
- Country of Publication:
- United States
- Language:
- English
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