Methanol → 4-(4-Tert-butoxycarbonylamino-naphthalen-1-yloxy)-pyrimidine-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of [4-(2-iodo-pyrimidin-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester (100 mg, 0.44 mmol) in 2 mL of DMF, was added, 0.5 mL MeOH, 0.12 mL of Et3N (0.9 mmol), Pd(OAc)2 (10 mg, 0.04 mmol), and DPPF (44 mg, 0.4 mmol). The reaction was heated under a CO balloon at 60° C. for 5 h. The reaction was then diluted with EtOAc, concentrated in vacuo on silica gel and chromatographed directly with 10-80% EtOAc-hexanes to provide 26 mg (14%) of 4-(4-tert-butoxycarbonylamino-naphthalen-1-yloxy)-pyrimidine-2-carboxylic acid methyl ester as a brown solid.

Provenance & Evidence