[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][N:3]=1.[H-].[Na+].C1(=O)O[CH2:18][CH2:17][O:16]1>CN(C=O)C.O>[CH3:1][C:2]1[N:3]([CH2:18][CH2:17][OH:16])[N:4]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=1A solution of 497 mg (3.14 mmol) of 3-methyl-5-phenylpyrazole in 12.6 mL of DMF at 0° C. was treated with 138 mg (3.45 mmol, 60% in oil) of NaH. After stirring for 15 min, 1.38 g (15.7 mmol) of ethylene carbonate was added, and the reaction was warmed to 25° C. and stirred overnight. The reaction was diluted with H2O and the product was extracted with hexanes/EtOAc (1:1). The combined organics were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography using hexanes/EtOAc (1:3) as eluent to give 305 mg (48%) of title compound: low resolution MS (ES) m/e 225 (MNa+), 203 (MH+).
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