Tetrahydrofuran → 2-[4-(4-Fluorophenoxy)phenyl]pyrimidine-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-[4-(4-Fluorophenoxy)phenyl]-4-methylpyrimidine: A 1M solution of potassium tert-butoxide in THF (11 mL, 11 mmol) was added via syringe to a solution of 4-(4-fluorophenoxy)benzamidine acetate (2.92 g, 10.2 mmol) in DMF. The resulting mixture was heated at 100° C. for 2 hours. Acetylacetaldehyde dimethyl acetal (2 mL, 13.6 mmol) was added via syringe. The reaction was maintained between 100°-110° C. overnight when TLC indicated complete reaction. The reaction was allowed to cool to room temperature and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water (3 times), dried over MgSO4, filtered, and evaporated under reduced pressure to give the desired product as a yellow oil. 1H NMR (CDCl3): δ8.60 (d, J=5.1, 1H), 8.40 (d, J=9.0, 2H), 7.05-7.00 (m, 7H), 2.57 (s, 3H). This material was carried on without further purification.

Provenance & Evidence