N-bromobutanimide → 6-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-amino-1-methyluracil (14.0 g, 100 mmol), N-bromosuccinimide (21.0 g, 118 mmol), and dry DMF (250 mL) was heated at 80° C. for 3 h. The reaction mixture was evaporated in vacuo and the residue was slurried with ice-cold 50% aqueous ethanol (150 mL) and filtered. The resulting off-white solid was washed with ethanol, then ether and dried to yield 18.0 g 2a (83%). mp 274° C. dec; UV pH 1 λmax 276 nm; NMR δ (DMSO-d6) 3.26 (s, 3H, CH3), 7.02 (s, 2H, NH2), 10.89 (s, 1H, NH).

Provenance & Evidence