
TY  - JOUR
A1  - Dickinson, RG 
A1  - Jacobsen, NW 
T1  - The hydrazinolysis of heterocyclic compounds. II. 6-Amino-4-hydroxy-1-methylpyrimidine-2(1H)-thione and related compounds
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1975
VL  - 28
IS  - 11
SP  - 2435
EP  - 2446
KW  - 
UR  - https://doi.org/10.1071/CH9752435 
N2  - The reaction of 6-amino-4-hydroxy-1-methylpyrimidine-2(1H)-thione (3) with hydrazine is shown to follow at least three pathways to give 4- amino-5-hydrazino-1,2,4-triazole-3-thiol (1), 5-hydrazino-pyrazol-3- ol(5; R = NH2), (4-amino-5-mercapto-1,2,4-triazol-3-yl)acetohydrazide (4) and triamino-guanidine (6). Similarly, 4,6-dihydroxy-1- methylpyrimidine-2(1H)-thione (18) yields (1) and malonyl dihydrazide (19), and (4). By contrast 4,6-diamino-1-methylpyrimidine-2(1H)-thione (21) does not follow any of these pathways. Formation of (4) represents a new type of ring transformation of pyrimidines. Mechanisms of the reactions are discussed. 
ER  -

