Pyridine → Tert-butyl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate

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Reaction Steps

A suspension of 2,2,2-trimethylacetamide (0.192 g, 1.897 mmol) in DCE (5 mL) was treated with oxalyl chloride (0.160 mL, 1.897 mmol), stirred at RT for 10 min, then heated at 80° C. for 1 h. The mixture was cooled to RT, added to a solution of tert-butyl (4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)carbamate (0.400 g, 1.264 mmol) and pyridine (0.112 mL, 1.391 mmol) in THF (10 mL) and stirred at RT overnight. The mixture was concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford tert-butyl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (367 mg, 65%). MS (ESI) m/z: 444.3 (M+H+).

Provenance & Evidence