Ethanol → 1-(2-(4-(5-Aminobenzo[b]thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione

Participants

Reaction Steps

A mixture of 1-(2-(5-bromo-4-(5-nitrobenzo[b]thiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (996 mg, 1.97 mmol), ethanol (100 mL) and indium powder, 100 mesh (1.13 g, 9.85 mmol) was heated to reflux with stirring. After 1.5 h the reaction mixture was cooled to r.t., diluted with water (40 mL) and filtered through a pad of celite. The yellow precipitate (collected on the celite) was purified by reverse phase chromatography (0.1% TFA in AcCN:H2O/10:90 to 95:5). The product fractions were combined, then passed through a 1 g SCX cartridge. The fully loaded cartridge was then washed with MeOH (4 mL) and 2 M ammonia in MeOH (8 mL). Elution of the desired compound was brought about by washing the cartridge finally with DMSO (4 mL). The solvent was removed in vacuo, employing a Genevac, to yield the title compound (142 mg, 15%) as a yellow amorphous solid. 1H NMR: δ (d6-DMSO, 400 MHz) 1.29 (s, 6 H), 3.39-3.54 (m, 4 H), 5.20 (s, 2 H), 6.83 (d, J=8.61 Hz, 1 H), 7.02 (s, 1 H), 7.62 (d, J=8.61 Hz, 1 H), 7.68 (s, 1 H), 8.38 (s, 1 H), 8.48 (s, 1 H), 10.82 (s, 1 H).

Provenance & Evidence