Sodium hydride → 1-Benzyloxypropanesulfamic acid[6-(2-(5-bromopyrimid-2-yloxy)-ethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyloxypropanesulfamic acid[6-(2-hydroxyethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide (237 mg, 0.441 mmol) in THF (10 mL) is added NaH (58 mg, 60% dispersion in mineral oil, 1.32 mmol). The mixture is stirred for 5 min before 2-chloro-5-bromopyrimidine (128 mg, 0.662 mmol) is added. The reaction mixture is stirred at 60° C. for 2 h, diluted with 10% aq. citric acid solution (75 mL) and extracted with EA (75 mL). The organic extract is washed twice with water (2×50 mL) and concentrated. The remaining residue is purified on prep. tlc plates (silica gel, heptane/EA 1:1) to afford 1-benzyloxypropanesulfamic acid[6-(2-(5-bromopyrimid-2-yloxy)-ethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide (283 mg) as a colourless foam. LC-MS: tR=1.09 min, [M+H]+=693.12; 1H NMR (CDCl3): δ 8.48 (s, 2H), 8.34 (s, 1H), 7.58-7.53 (m, 2H), 7.38-7.28 (m, 5H), 7.16-7.11 (m, 2H), 6.84 (s, 1H), 5.97 (t, J=5.9 Hz, 1H), 4.73-4.68 (m, 2H), 4.64-4.60 (m, 2H), 4.50 (s, 2H), 3.56 (t, J=5.9 Hz, 2H), 3.17 (q, J=6.4 Hz, 2H), 1.88 (p, J=5.9 Hz, 2H).

Provenance & Evidence