1,3-Dibromo-5,5-dimethylhydantoin → Tert-butyl 2-[(4-amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)carbonyl]morpholine-4-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 2-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)carbonyl]morpholine-4-carboxylate (0.66 g, 1.90 mmol) in THF (5 mL) was cooled to −50° C. and stirred for 1 h before adding 1.3-dibromo-5,5-dimethylhydantoin (0.27 g, 0.94 mmol) in portions. The reaction was then quenched with satd. Na2SO3 solution. The product was extracted with EtOAc, dried (MgSO4) and concentrated. The crude solid was triturated with EtOAc and filtered. An off-white solid was isolated (530 mg, 65%). 1H-NMR (DMSO-d6) δ 8.10 (s, 1 H), 7.54 (s, 1 H), 5.05-4.95 (m, 1 H), 4.00-3.89 (m, 2H), 3.69-3.55 (m, 2 H), 3.10-3.00 (m, 2 H), 1.33 (bs, 9 H).

Provenance & Evidence