CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH2:37][OH:38])=[CH:31][CH:30]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[N:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH:37]=[O:38])=[CH:31][CH:30]=1A mixture of the Dess-Martin reagent (1.59 g, 3.75 mmol) and 3-[4-(2-pyrimidinyl)phenyl]-2-propyn-1-ol (525 mg, 2.50 mmol, prepared as described in Reference Example 239) in dichloromethane (15 mL) was stirred at room temperature for 30 min. Aqueous 10% Na2S2O3 (25 mL) and aq. sat. NaHCO3 (15 mL) were added, the mixture was stirred for 5 min, the layers were separated, and the aqueous layer was extracted with dichloromethane (10 mL). The combined organic layers were dried (MgSO4) and concentrated to provide 465 mg (89%) of the title compound as a yellow solid. MS 209 (M+H)+.
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