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

Participants

Reaction Steps

A solution of 2,2,2-trimethylacetamide (0.750 g, 7.42 mmol) in DCE (10 mL) was treated with oxalyl chloride (0.600 mL, 7.09 mmol), stirred at RT for 10 min, then heated at 80° C. for 1 h. The mixture was cooled to RT, partially concentrated, then added drop-wise to a solution of tert-butyl (4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)carbamate (1.6 g, 5.29 mmol) in pyridine (0.60 mL, 7.44 mmol) and stirred at RT for 45 min. The mixture was concentrated to dryness, treated with MeCN, sonicated and the solids collected via filtration. The filtrate was concentrated to dryness, suspended in MeCN, sonicated, the resulting solid collected via filtration and combined with the above-isolated solid to afford tert-butyl (4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (1.6 g, 70%). MS (ESI) m/z: 430.2 (M+H+).

Provenance & Evidence