Optimisation of the Synthesis of Guanidines from Amines via Nitroguanidines Using 3,5-Dimethyl-N-nitro-1H-pyrazole-1-carboxamidine

Abstract

The synthesis of the useful reagent for the preparation of guanidines, 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine (DMNPC), has been optimised. A detailed protocol for using this reagent for the preparation in pure form of a range of guanidines via nitroguanidines is described. A comparison has been made regarding efficiency between DMNPC and the guanidinylating reagents N,N′-bis-Boc-1-pyrazole-1-carboxamidine (2) and N,N′-bis-Boc-N′-triflylguanidine (3).

Key words

guanidinylation - 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine - hydrogenolysis - ion exchange chromatography

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