Water → 4-(1-Isopropyl-2-methylimidazol-5-yl)-2-[4-(3-morpholinopropylsulphonyl)anilino]pyrimidine

Participants

Reaction Steps

A solution of water (0.5 ml) and oxone (400 mg) was added to a solution of 4-(1-isopropyl-2-methylimidazol-5-yl)-2-[4-(3-morpholinopropylthio)anilino]pyrimidine (Method 85; 260 mg, 0.58 mmol) in MeOH (2.5 ml) and acetone (0.5 ml). The mixture was stirred for 4 hours, a solution of sodium metabisulphite (250 mg) in water (1 ml) was added and the mixture stirred for a further 20 minutes. The volatiles were removed by evaporation. Water (10 ml) was added to the residue and saturated aqueous sodium hydrogen carbonate solution added to basify the solution. The aqueous solution was extracted with EtOAc (2×25 ml), the extracts combined, washed with brine (10 ml), dried and evaporated. The residue was purified by chromatography on silica eluting with DCM/MeOH (98:2 increasing in polarity to 92:8). The purified product was dissolved in methanol (4 ml), 1M ethereal hydrogen chloride (270 μl) added and the volatiles removed by evaporation. The residue was triturated with ether to give the title compound (120 mg, 43%). NMR: 1.52 (d, 6H), 1.98 (br t, 2H), 2.62 (s, 3H), 2.88-3.00 (br m, 6H), 3.33 (t, 2H), 3.77 (br s, 4H), 5.53 (sept, 1H), 7.20 (d, 1H), 7.69 (s, 1H), 7.81 (d, 2H), 7.98 (d, 2H), 8.58 (d, 1H), 9.77 (s, 1H); m/z 485.

Provenance & Evidence