N#N.[Si:3]([O:10][CH2:11][C:12]1[S:16][C:15]([CH2:17][OH:18])=[N:14][CH:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:19]I>C(Cl)Cl>[Si:3]([O:10][CH2:11][C:12]1[S:16][C:15]([CH2:17][O:18][CH3:19])=[N:14][CH:13]=1)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (5-(((tert-butyldimethylsilyl)oxy)methyl)thiazol-2-yl)methanol (1.21 g, 4.65 mmol) in CH2Cl2 (3.0 mL) was treated with MeI (0.35 mL, 5.57 mmol) followed by Ag2O (1.61 g, 6.97 mmol) and the resulting mixture (protected from light) was stirred overnight at 40° C. The reaction mixture was filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (4:1 hept-EA)=0.27. LC-MS-conditions 07: tR=0.99 min, [M+H]+=273.95.
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