Dimethylformamide → HCID 13208054, compound

Participants

Reaction Steps

In N,N-dimethylformamide (20 ml) and 2 N NaOH (5 ml) was dissolved 4-(2-chloro-6-fluorobenzyl)amino-6-methylamino-5-phenylazopyrimidine (1.112 g, 3 mmols), and sodium dithionite (3.27 g, 15 mmol; purity 80%) was added portionwise to the solution with stirring at 140°-150° C. The mixture was stirred at the same temperature for 30 minutes, after which it was concentrated to dryness under reduced pressure, and water was added to the residue. The mixture was adjusted to pH 12-13 by addition of 2 N NaOH, and extracted with ethyl acetate (150 ml, 100 ml). The extract was dried over anhydrous sodium sulfate. The ethyl acetate was evaporated under reduced pressure, and the resultant residue was recrystallized from ethyl acetate-petroleum ether to give 5-amino-4-(2-chloro-6-fluorobenzyl)amino-6-methylaminopyrimidine as brown crystals (671 mg, yield 79%), m.p. 210°-213° C.

Provenance & Evidence