Methanol → 1-Hydroxypropanesulfamic acid[6-(2-(5-bromopyrimid-2-yloxy)-ethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide

Participants

Reaction Steps

A solution of 1-benzyloxypropanesulfamic acid[6-(2-(5-bromopyrimid-2-yloxy)-ethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide (283 mg, 0.408 mmol) in DCM (15 mL) is cooled to −78° C. an then slowly treated with BBr3 (0.816 mL of a 1 M solution in DCM). The reaction mixture is allowed to warm to rt and stirring is continued for 1 h. Methanol (approx. 10 mL) is added to the suspension and stirring is continued for another 10 min before the mixture is diluted with 10% aq. citric acid solution (75 mL) and extracted with DCM (2×75 mL). The organic extracts are washed with water (50 mL), dried over MgSO4, filtered and concentrated. The crude product is purified on prep. tlc plates (silica gel, DCM with 10% methanol) to afford 1-hydroxypropanesulfamic acid[6-(2-(5-bromopyrimid-2-yloxy)-ethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide (223 mg) as a pale grey foam. LC-MS: tR=0.92 min, [M+H]+=602.87; 1H NMR (CDCl3): δ 8.48 (s, 2H), 8.44 (s, 1H), 7.58-7.54 (m, 2H), 7.18-7.13 (m, 2H), 6.91 (s, 1H), 5.93 (t, J=6.4 Hz, 2H), 4.75-4.70 (m, 2H), 4.65-4.60 (m, 2H), 3.75 (t, J=5.2 Hz, 2H), 3.17 (q, J=6.4 Hz, 2H), 1.85-1.76 (m, 3H).

Provenance & Evidence