Potassium Carbonate → HCID 69518541, compound

Participants

Reaction Conditions

Reaction Steps

To the mixture of 172 mg (0.54 mmol) of Ethyl 6-ethyl-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate and 320 mg (1.95 mmol) of potassium carbonate in 3 mL of anhydrous dimethylformmamide was added 270 uL (2.3 mmol) of 4-chloro-2-methylthiopyrimidine. The mixture was heated at 130° C. for half an hour. After cooling to room temperature, the reaction was dumped into 50 mL of brine, the product was extracted with ethyl acetate. The combined organic phases were washed with brine, and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified by silica chromatography with 1:9 EtOAc/Hexane (1:9) to afford 102 mg (43%) of a yellow solid: 1H NMR (CDCl3/400 MHz) 8.35(d, 5.2 Hz, 1H), 7.72(s, 1H), 7.13(s, 1H), 6.74(s, 1H), 6.54(d, J=5.6 Hz, 1H), 5.66(q, J=6.8 Hz, 1H), 4.30(m, 2H), 2.45(q, J=7.6 Hz, 2H), 2.27(s, 3H), 1.33(t, J=7.2 Hz, 3H), 1.12(t, J=7.6 Hz, 3H); MS (ESI+) 441 (M+1, 100).

Provenance & Evidence