Cesium carbonate → t-Butyl(4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of t-butyl (4-hydroxy-1-naphthyl)carbamate (5.0 g, 19.3 mmol), 4-iodo-2-methylthiopyrimidine (4.86 g, 19.3 mmol) and cesium carbonate (7.52 g, 23.1 mmol) in DMF (25 ml) is heated at 70° C. for 20 h. The resulting mixture is diluted with CH2Cl2 (50 ml), washed with water (25 ml×3), dried over Na2SO4 and concentrated. This residue is dissolved in minimum volume of EtOAc at 70° C. and then hexane (20 ml) is added. The resulting solution is left at room temperature overnight, filtered and washed with hexane to obtain t-butyl(4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)carbamate as a pink solid (4.2 g); Mp: 173-174° C.; 1H NMR (300 MHz, CDCl3) δ 1.56(s, 9H), 2.30(s, 3H), 6.45(d, J=5.7 Hz, 1H), 6.86(s, 1H), 7.27(d, J=8.1 Hz, 1H), 7.47-7.60(m, 2H), 7.87-7.94(m, 3H), 8.32(d, J=5.7 Hz, 1H); MS: 384 (M+1).

Provenance & Evidence