Hydrochloric Acid → 1-amino-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)-phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

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Reaction Steps

A suspension of 3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-1-[(1-methylethylidene)-amino]-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.300 g, 0.60 mmol), 1 N HCl (3.0 mL,), and methanol (3.0 mL) was heated to reflux for 2 hours. The reaction was cooled to room temperature, partitioned between water and ethyl acetate, and the phases separated. The aqueous phase was extracted ethyl acetate (3×50 mL) and concentrated. Chromatography (20% ethyl acetate/hexane) of the residue afforded 1-amino-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)-phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 0.12 g (43.5%) of a white solid. 1H-NMR (CDCl3): δ 4.58 (bs, 2H), 6.25 (s, 1H), 6.94 (dd, J=8.38, 1.13 Hz, 1H), 7.03 (d, J=6.52 Hz, 1H), 7.24 (dt, J=7.29, 1.22 Hz, 1H), 7.43 (d, J=8.83 Hz, 1H), 7.53 (dt, J=7.12, 1.69 Hz, 1H), 7.97 (dd, J=8.15, 1.65 Hz, 1H).

Provenance & Evidence