Sodium ethoxide → HCID 42626124, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-(4-aminophenoxy)-2-aminopyridin-3-yl-methyl-carbamate (180 mg, 0.6 mmol) was suspended in a solution of sodium ethoxide in ethanol, obtained from dissolving sodium (480 mg, 21 mmol) in ethanol (9 ml). The suspension was heated under microwave irradiation for 40 minutes (100° C., 150 W). The mixture was cooled at room temperature, diluted with water and evaporated. The residue was triturated with acetone, and the washings discarded. The solid was dissolved in water and the insoluble solid was filtered off. The filtrate was acidified with HCl 1 M to pH 1, then brought to pH 10 with saturated aqueous Na2CO3. The precipitate formed was recovered by filtration, to afford the title compound (52 mg, 34%). 1H-NMR (δ, ppm, DMSO-d6): 3.49 (s, 3H, CH3N), 5.11 (s, 2H, NH2), 6.29 (d, 1H, HPy,6, J=6.0 Hz), 6.63 (d, 2H, Harom,Ph,3+5, J=8.69 Hz), 6.90 (d, 2H, Harom,Ph,2+6, J=8.73 Hz), 7.74 (d, 1H, HPy,6, J=5.96 Hz), 11.53 (s, 1H, NHPy2). LC-MS (m/z): 257 (M+H, 100).

Provenance & Evidence