Hydrochloric Acid → Tert-butyl 2,4-dimethoxybenzyl6-amino-1-methyl-1h-imidazo[4,5-c]pyridin-4-ylcarbamate

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Reaction Steps

In a 1000 mL round bottom flask, tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate (example 1C, 9.2 g, 15.93 mmol) was stirred in THF (50 mL). 1 N HCl (33 mL) was added. After 2 min, the reaction was quenched with 1 N NaOH (65 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was dried under vacuum for 1 h and triturated with ether (4×). Isolated tert-butyl 6-amino-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(2,4-dimethoxybenzyl)carbamate (6.587 g, 15.93 mmol, 100% yield) as a cream solid. Material carried forward with no further purification.

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