Ethyl Acetate → HCID 68288489, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)carbamate (31) (250 mg, 0.67 mmol), and N,N-dimethylguanidine sulfate (220 mg, 0.8 mmol) in ethanol (10 ml) was added 21% wt sodium ethoxide in ethanol (218 μl, 0.67 mmol). The mixture was heated to 80° C. for 24 hours followed by addition of N,N-dimethylguanidine sulfate (110 mg, 0.4 mmol) and 21% wt sodium ethoxide in ethanol (100 μl). After a further 2 days at 80° C. the mixture was poured into ethyl acetate (150 ml) washed with water (100 ml), brine (100 ml) and dried over anhydrous magnesium sulfate. Evaporation to dryness yielded tert-butyl (3-(2-(dimethylamino)pyrimidin-4-yl)-7-methoxynaphthalen-1-yl)carbamate (140) as a pale brown foam (261 mg). 1H NMR (CDCl3) 400 MHz δ 8.41-8.36 (m, 3H), 7.88-7.87 (d, J=8.8 Hz, 1H), 7.52 (m, 2H), 7.19 (dd, J=2.4 and 9.2 Hz 1H), 7.13 (m, 1H), 7.02 (d, J=5.6 Hz, 1H) 6.65 (s, 1H), 3.97 (s, 1H), 3.31 (s, 6H), 1.57 (s, 9H), LCMS m/e 395 (M+H)

Provenance & Evidence