Tert-butyl (3-((5-(hydroxymethyl)-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate → Tert-butyl (3-((5-formyl-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate

Beteiligte Stoffe

Reaktionsschritte

At RT, manganese (IV) oxide (358 g, 4.1 mol) was added to a solution of tert-butyl (3-((5-(hydroxymethyl)-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate (50d) (140 g, 386.8 mmol) in CHCl3. After 18 h, the reaction mixture was filtered through a pad of Celite washing with 3×100 mL of CHCl3. The filtrate was concentrated and the residue was purified on a silica gel column (eluted with 15-65% EtOAc in hexanes) to give tert-butyl(3-((5-formyl-2-(methylthio)pyrimidin-4-yl)amino)phenyl)carbamate (60 g, 43% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.61 (1H, br. s.), 9.77 (1H, s), 8.44 (1H, s), 7.99 (1H, br. s.), 7.33-7.39 (1H, m), 7.27-7.30 (1H, m), 7.00-7.06 (1H, m), 6.41-6.55 (1H, m), 2.59 (3H, s), 1.53 (9H, s). m/z (ESI, +ve ion) 361.1 (M+1)+.

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