p-Toluenesulfonic acid → HCID 178458660, compound

Participants

Reaction Steps

To a solution of 6-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-5-fluoro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N4-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (Example 25; 0.21 g, 0.415 mmol) in methanol (5 ml) was added a few drops of water and then p-toluenesulfonic acid (0.119 g, 0.623 mmol). The mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was subjected to silica gel chromatographic purification (by ISCO Combiflash with gradient EtOAc/hexanes) to afford the desired product as a white solid (0.075 g, yield 40%). LC-MS, 466 (M+1); 1H NMR δ 9.85 (br s, 1H), 8.30 (s, 1H), 7.60 (m, 1H), 7.30 (m, 1H), 5.25 (s, 1H), 4.80-4.90 (m, 2H), 4.60 (m, 2H), 4.0 (br s, 2H), 3.55 (m, 1H), 1.35 (d, 3H), 1.15 (d, 6H).

Provenance & Evidence