反应详情

温度

70 °C

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, 9 H), 2.30 (s, 3H), 6.45 (d, J=5.7 Hz, 1H), 6.86 (s, 1H), 7.27 (d, J=8.1Hz, 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).

1. washwashed with water (25 ml×3)
2. dry with materialdried over Na2SO4
3. concentrationconcentrated
4. dissolutionThis residue is dissolved in minimum volume of EtOAc at 70° C.
5. additionhexane (20 ml) is added
6. filtrationfiltered
7. washwashed with hexane