[Br:1][C:2]1[N:3]=[C:4]([CH3:9])[NH:5][C:6]=1[CH2:7][OH:8].C(Cl)Cl>[O-2].[O-2].[Mn+4].O1CCOCC1>[Br:1][C:2]1[N:3]=[C:4]([CH3:9])[NH:5][C:6]=1[CH2:7][OH:8].[Br:1][C:2]1[N:3]=[C:4]([CH3:9])[NH:5][C:6]=1[CH:7]=[O:8]4-Bromo-5-hydroxymethyl-2-methylimidazole was prepared according to the procedure described by S. P. Watson, Synthetic Communications, 22, 2971-2977 (1992). A solution of 4-bromo-5-hydroxymethyl-2-methylimidazole (4.18 g, 21.9 mmol) was refluxed with manganese dioxide (16.1 g) in 1:1 methylene chloride:dioxane (200 mL) for 16 h. The cooled reaction was filtered through celite and concentrated to yield the title compound as a pale yellow solid. 1H NMR (CDCl3, 300 MHz) δ 9.57 (1H, s), 2.52 (3H, s).
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