Pyrimidine, 6-amino-4-hydrazino-2-methyl

Pyrimidin 2-Amino-6-chlor-4-(l-methyl-hydrazino)- El6a, 731 (Cl - NR-NH2)... 

H-< 1,2,4-Oxadiazolo[4.3-a]-l,3,5-triazin) 5,7-Dimethyoxy-3,3-dimethyl- E16c, 221 (aus Azido-1.3,5-triazin) Pyrimidin 5-Ethoxycarbonyl-4-hydrazino-2-hydroxy-6-methyl-E16a, 766 (SH - NH-NH2) 2H-l,2,3-Triazol 5-(Diethoxy-methylen-amino)-4-formyl- E4, 565 [C(OR)4 + Amin]... 

Phenacyl bromides react (86JHC43) with anhydro l-amino-5-aryI-2-mercapto-l,2,4-triazolo[3,2-c]quinazolin-4-ium hydroxides (53) through pyrimidine ring-opening and simultaneous formation of the 1,3,4-thiadiazine nucleus to give 54. Compound 514 was also obtained [86JAP(K)61260085] when 2-hydrazino-5-methyl-6/f-l,3,4-thiadiazine (513) was cyclized with aryloxyacetyl chlorides. 

Thus, the reaction with methylamine at room temperature furnishes the 2-(methylamino)-3-methyl derivative, that with benzylaminc two products, the 3-benzyl-2-(benzylamino)-2-ethoxy derivative and the 3-benzyl-2-(benzylamino) derivative, and that with hydroxylamine the corresponding 2-ethoxy-3-hydroxy derivative. Similarly, with hydrazine hydrate at room temperature, ethyl 3-[(ethoxythiocarbonyl)amino]pyridine-2-carboxylate is transformed into 3-amino-2-sulfanylpyrido[3,2-c/]pyrimidin-4(3//)-one (8), whilst under reflux the 2-hydrazino compound is obtained. 

Gyanogen chloride bubbled during ca. 0.5 hr. at 25-30° into 4-hydrazino-6-methyl-2-ethylpyrimidine in N HGl, stoppered, and allowed to stand 1 hr. at room temp. 2-amino-5-ethyl-7-methyl-s-triazolo[2,3-c]pyrimidine. Y 82%.— Isomerization of the intermediate s-triazolo[4,3-c] pyrimidines occurs by heat or strong alkali or acids. F. e. s. G. W. Miller and F. L. Rose, Soc. 1963, 5642. 

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