N,N'-Dimethylethylenediamine → 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methyl-1-(3-thienyl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A degassed solution of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one (26 mg, 0.097 mmol), 3-iodothiophene (23 mg, 0.102 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), copper iodide (4 mg, 0.020 mmol), and potassium phosphate (41 mg, 0.194 mmol) in 2 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (16 h) at 70° C., the reaction was complete and therefore allowed to cool to room temperature. The reaction was extracted with with EtOAc (3×5 mL) and with NaHCO3 (2×10 mL). The crude organic layers were combined, dried over anhydrous Na2SO4 (s), filtered and then concentrated in vacuo. The crude mixture was then purified over silica using a 0-100% EtOAc gradient/100-0% Hexane gradient mixture after which, the appropriate fractions were concentrated to afford a solid. This solid was further purified by recrystallization using an Et2O/Hexane solvent mixture to give the title compound (11 mg, 35%). 1H NMR (DMSO) δ: 7.98 (s, 1H), 7.92 (s, 1H), 7.84 (d, J=6.2, 1H), 7.22 (d, J=6.2, 1H), 6.28 (m, 1H), 6.17 (d, J=7.0 Hz, 2H), 3.98 (br. S, 2H), 3.33 (s, 2H), 2.56(t, j=5.3 Hz, 2H), 2.17 (s, 3H)

Provenance & Evidence