1,1'-Carbonyldiimidazole → 1-(4-((2-Aminopyridin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea

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Reaction Steps

To a solution of 1,1′-carbonyldiimidazole (CDI) (4.18 g, 25.80 mmol) in DCM (15 mL) was added dropwise under nitrogen a solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (6) (5.91 g, 25.80 mmol) in DCM (15 mL) over 40 mins. The resulting solution was stirred at RT for 1 h and then added dropwise under nitrogen to a solution of 2-amino-4-[(4-aminonaphthalen-1-yloxy)methyl]pyridine (4) (3.80 g, 12.89 mmol). The mixture was stirred overnight and the volatiles were then removed in vacuo. The crude material was purified by flash chromatography (Biotage 120 g); eluting with 0 to 6% MeOH in DCM to give 1-{4-[(2-aminopyridin-4-yl)methoxy]naphthalen-1-yl}-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea (5) (4.27 g, 63%): m/z 521 (M+H)+ (ES+).

Provenance & Evidence