Ammonium Chloride → 6-[2-(Tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-pyridin-3-ylamine

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Reaction Steps

To a solution of 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-3-nitro-pyridine (80, 2.67 g, 8.1 mmol) in 15 mL THF, zinc dust (1.6 g, 24 mmol) followed by 8.2 mL (8.2 mmol) 1M NH4Cl solution was added. After stirring at room temperature for 3 h, more zinc dust (0.77 g, 8.13 mmol) and NH4Cl (0.43 g, 8.31 mmol) was added. After stirring for 4 h at mixture was filtered through celite and filtrate was extracted with CH2Cl2 and 1M NaOH. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (Hexane/AcOEt 3:1→2:1) to give 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-pyridin-3-ylamine as a yellowish oil (1.3 g, 54%). Exact mass calculated for C25H34BrN5O5 563.17. found 564.3 (MH+).

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