Hydrazine hydrate (1:1) → 2-Hydrazinyl-4-methylpyrimidine

Participants

Reaction Conditions

Reaction Steps

Based on a reported procedure (Vanderhaeghe, Claesen, Bull. Soc. Chim. Belg. 1959, 68, 30). Hydrazine monohydrate (334.7 ml, 6.90 mmol) was added in one portion to a solution of 4-Methyl-2-methylsulfanyl-pyrimidine (357.9 g, 2.55 mol) in abs. EtOH (890 ml). The resulting mixture was refluxed for 50 h, then hydrazine monohydrate (200 ml) was added and refluxing was continued for 50 h (the reaction was monitored by 1H NMR). Then it was cooled to 0° C. to crystallize and 213 g of crude product was isolated by filtration. Recrystallization from ethanol gave the title compound (184.7 g, 59%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ, ppm: 2.40 (s, 3H), 4.00 (broad, 2H), 6.512 (d, 1H, 5 Hz), 7.03 (broad, 1H), 8.24 (d, 1H, 5 Hz).

Provenance & Evidence