1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-6-methyl-7-(1,4-oxazepan-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Participants

Reaction Steps

To a stirring solution of chloroform (20 mL) and 6-methyl-7-(1,4-oxazepan-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (650 mg, 2.49 mmol), at −40° C., was added 1,3-dibromo-5,5-dimethylhydantoin (356 mg, 1.24 mmol). The mixture was allowed to stir for 10 minutes while warming to rt. The mixture was partitioned between ethyl acetate (200 mL) and saturated aqueous Na2CO3 solution (150 mL). The layers were separated and the organic phase was washed with brine, dried (Na2SO4), and concentrated to dryness. Trituration with acetonitrile afforded 500 mg (59%) of the desired product. 1H-NMR (DMSO-d6) δ 7.82 (s, 1H), 3.91 (s, 2H), 3.62 (t, J=5.4 Hz, 2H), 3.55-3.53 (m, 2H), 2.61-2.56 (m, 4H), 2.15 (s, 3H), 1.77-1.72 (m, 2H); MS [M+H]+=339.9, 341.9; LCMS RT=1.09.

Provenance & Evidence