Improved syntheses in the pyrimidine series. VI. 4‐amino‐3‐methyl‐5‐nitro‐2‐pyrimidone and some of its purine and pteridine derivatives
1959; Wiley; Volume: 9; Issue: 4 Linguagem: Inglês
10.1002/jctb.5010090402
ISSN1934-998X
Autores Tópico(s)Chemical Synthesis and Analysis
ResumoAbstract A direct route from nitroacetonitrile to 3‐methyl‐5‐nitrocytosine ( II ; R=NO 2 ) is described. This led to the preparation of the long‐sought 5‐amino‐3‐methylcytosine and the purines and pteridines derivable from it. The structure of the nitro compound was rigorously confirmed by comparison with other isomers and by conversion (after reduction of the nitro group) into 1‐methy1–2‐pteridone, its 6:7‐dimethyl derivative, and into 8‐hydroxy‐3‐methyl‐2‐purinone. Isomers corresponding to these were prepared independently for comparison. Attempted conversion with carbon disulphide and pyridine, into 8‐mercapto‐3‐methyl‐2‐purinone however gave a rearranged product, shown to be 2‐hydroxy‐8‐mercapto‐9‐methylpurine by unambiguous synthesis. Ultra‐violet spectra and ionisation constants are tabulated.
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