Methanol → HCID 22273524, compound

Participants

Reaction Conditions

Reaction Steps

Sodium t-butoxide (1.04 g, 10.8 mmol) was added to a degassed solution of 2-amino-4-(1,2-dimethylimidazol-5-yl)pyrimidine (Method 26; 567 mg, 3 mmol), N-(2-methoxyethyl)-4-iodobenzenesulphonamide (Method 40; 1.54 g, 4.5 mmol), tris(dibenzylideneacetone) dipalladium (0) (72 mg, 0.15 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (102 mg, 0.15 mmol) in dioxane (36 ml) and the mixture heated at 80° C. overnight. The reaction was cooled to room temperature and MeOH (5 ml) was added and the mixture poured onto an Isolute SCX-2 column, eluted first with MeOH (10×30 ml) and the product was then eluted with 2% methanolic ammonia (10×30 ml). The solvent was removed by evaporation and the residue was dissolved in EtOAc (100 ml), washed with water (3×100 ml) and then brine (100 ml), dried and the solvent removed by evaporation to give the title compound (1.01 g, 84%) as a foam. NMR 2.40 (s, 3H), 3.07 (q, 2H), 3.20 (s, 3H), 3.38 (t, 2H), 3.86 (s, 3H), 5.00 (t, 1H), 6.95 (d, 1H), 7.47 (s, 2H), 7.71 (m, 4H), 8.36 (d, 1H); m/z 403.

Provenance & Evidence