A study of certain reactions of 4-chloro-6-methylhydrazino-5-nitropyrimidine and the 4-methoxy and 6-dimethylamino analogs Public Deposited

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  • The reaction between 4- chloro- 6- methoxy- 5-nitropyrimidine and methylamine was investigated. The reaction product was identified as 4-methoxy-6-methylamino-5-nitropyrimidine from synthesis of the product via 4-chloro-6-methylamino-5-nitropyrimidine. The product was the result of displacement of chloro substituent with methylamine. The reaction occured under mild condition (e. g. 15-20 C. in dioxane). Reaction of 4-chloro-6-methoxy-5-nitropyrimidine with methylhydrazine does yield product as a result of direct nucleophilic substitution. When the 4-methoxy-6-methylamino-5-nitropyrimidine was refluxed with methylhydrazine in absolute methanol to yield a product, carbon-hydrogen-nitrogen analysis of this substance indicated that the compound was 4-methylamino-6-(l-methylhydrazino)-5-nitropyrimidine. During the course of a study involving the preparation of certain derivatives, 4-dimethylamino-6-methoxy-5-nitropyrimidine or 4-methylhydrazino analog was refluxed with methylhydrazine in pyridine there was no evidence of nucleophilic substitution of methoxy group; approximately 40% of starting material was recovered. The reason that 4-dimethylamino-6-methoxy -5-nitropyrimidine does not respond to direct nucleophilic substitution with methylhydrazine apparently stems from steric hindrance imposed by the methylhydrazine substituent. Among the effects caused by the steric crowding is the forcing of the nitro substituent out of the plane of the pyrimidine ring thus losing the important resonance contribution of the nitro substituent in making the 4- and 6-positions more electrophilic. The it spectral data are included for all previously unreported compounds which were prepared.
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