Sodium hydride → HCID 21865285, compound

Participants

Reaction Steps

To a 25-mL, round-bottomed flask containing 4-(4-tert-butyl-phenyl)-6-chloro-pyrimidine, (Example 1(a)), (0.20 g, 0.82 mmol), 3-methoxybenzenethiol (0.23 g, 1.6 mmol, Aldrich) and DMF (4 mL) under a N2 atmosphere at room temperature was added NaH (0.066 g, 1.6 mmol, 60% disp. in oil, Aldrich). The mixture turned green and gas evolution was observed. The solution was stirred for 20 h at room temperature under a N2 atmosphere. The reaction was quenched with H2O (50 mL), and the resulting solution was extracted with EtOAc (3×25 mL). The combined extracts were washed with H2O (3×25 mL) and brine, dried over Na2SO4, and adsorbed onto silica. The crude material was purified by chromatography (0 to 15% ethyl acetate/hexanes) on silica gel to afford the title compound as a colorless oil. MS (ESI, pos. ion.) m/z: 351.2 (M+1).

Provenance & Evidence