[CH3:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:5][C:6]1[NH:11][C:10](=[O:12])[NH:9][C:8](=[O:13])[C:7]=1[CH:14]([CH3:16])[CH3:15].[I-].[Li+].CS([CH2:27][C:28]#[CH:29])(=O)=O.[CH3:30]N(C=O)C>CCOCC>[CH2:27]([N:11]1[C:6]([O:5][C:4]2[CH:3]=[C:2]([CH3:1])[CH:19]=[C:18]([CH3:20])[CH:17]=2)=[C:7]([CH:14]([CH3:16])[CH3:15])[C:8](=[O:13])[NH:9][C:10]1=[O:12])[C:28]#[C:29][CH3:30]
To a stirred solution of 6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione (114) (548 mg, 2 mmol) anhydrous powdered K2CO3 (276 mg, 2 mmol), and lithium iodide (268 mg, 2 mmol) in DMF (10 mL), was added 1-methanesulfonyl-2-propyne (247 μL, 2.1 mmol). After stirring for 17 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, ethyl acetate:hexane (1:2)) to afford 546 mg (84%) of a white solid. m.p. 158-160° C.; 1H-NMR (200 MHz, CDCl3) δ1.15 (6H, d, J=7.0 Hz), 1.69 (3H, t, J=2.2 Hz), 2.32 (6H, s), 2.80 (1H, m), 4.43 (2H, q, J=2.2 Hz), 6.60 (2H, s), 6.78 (1H, s), 8.55 (1H, s); m/z (EI) 326(M+).
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