Hydrazine hydrate (1:1) → N-amino-N'-(2-chlorophenyl)pyrimidine-4-carboxamidine

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Reaction Steps

To a suspension of N-(2-chlorophenyl)pyrimidine-4-carboxamide 3 (0.2 g, 0.86 mmol) in 20 mL of PhMe was added 0.65 g of PCl5. The mixture was stirred at reflux for 3 h. To this solution was added 3 mL of NH2NH2.H2O. The mixture was stirred at ambient temperature for 2 h. After removal of all solvent, the residue was purified by column (2:1 of hexane/ethyl acetate) to give N-amino-N′-(2-chlorophenyl)pyrimidine-4-carboxamidine 5 as a solid. Yield: 0.15 g, 70%. 1HNMR (DMSO-d6) δ (ppm): 9.15 (s, 1H); 8.70 (d, 1H); 7.98 (d, 1H); 7.35 (m, 1H); 7.15 (m, 1H); 6.80 (m, 1H); 6.45 (d, 1H); 5.60 (s, 2H).

Provenance & Evidence