Potassium Carbonate → HCID 54059613, compound

Participants

Reaction Steps

To a stirred solution of 6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione (114) (prepared using the methods of WO9518109, herein incorporated by reference in its entirety for all purposes; 274 mg, 1 mmol) anhydrous powdered K2CO3 (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol) in DMF (5 mL), was added 1-methanesulfonyl-trans-2-butene (141 μL, 1.2 mmol). After stirring for 15 hrs., the reaction mixture was diluted with ether, washed with water, dried with MgSO4, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:dichloromethane:hexane (1:1:2)) to afford 247 mg (75%) of a white solid. m.p. 141-143° C.; 1H-NMR (200 MHz, CDCl3) δ1.13 (6H, d, J=7.0 Hz), 1.59 (3H, d, J=6.0 Hz), 2.29 (6H, s), 2.72 (1H, m), 4.20 (2H, d, J=5.5 Hz), 5.34-5.61 (2H, m), 6.51 (2H, s), 6.75 (1H, s), 9.00 (1H, s); m/z (EI) 328(M+).

Provenance & Evidence