1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Participants

Reaction Steps

To a solution of 7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (562 mg, 2.40 mmol) in THF (19 ml) at −20 C was added 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (344 mg, 1.2 mmol) in three portions. The reaction was stirred at −20 C for 3 h. Upon the completion, the reaction was quenched with aqueous saturated Na2SO3 and allowed to warm up to rt. The crude was extracted with ethyl acetate. The organic was washed with brine, dried over Na2SO4 and concentrated. The resulting crude was purified via column chromatography (95:5 v/v CH2Cl2—CH3OH) to afford 600 mg of the title compound as yellow solid (yield 79%). 1H-NMR (DMSO-d6) δ 7.84 (s, 1H), 6.71 (s, 1H), 3.74 (s, 2H), 3.51 (t, J=4 Hz, 4H), 2.37(t, J=4 Hz, 4H); MS [M+H]+=312; LCMS RT=1.04 min.

Provenance & Evidence