N,N'-Dimethylethylenediamine → 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methyl-1-(4-methylphenyl)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 (25 mg, 0.097 mmol), 1-iodo-4-methylbenzene (20 mg, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), Copper Iodide (5 mg, 0.024 mmol), and Potassium Phosphate (41 mg, 0.194 mmol) 2 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (17 h) at 70° C., the reaction was complete and allowed to cool to room temperature. The reaction was extracted 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 using the ISCO flash chromatography system using a CHCl3/EtOAc gradient. Upon reaching a 1:1 mixture of EtOAc and CHCl3, 3% MeOH was added and increased to 6% MeOH which, after concentrating the appropriate fractions afforded the title compound as a tan solid (13 mg, 38%). 1H NMR (DMSO) δ: 7.90 (s, 1H), 7.50-7.59 (m, 2H), 7.44 (d, J=6.7 Hz, 1H), 7.25-7.32 (m, 2H), 6.19 (s, 2H), 6.08 (d, J=7.0 Hz, 1H), 3.89 (br. S, H), 3.29 (s, 2H), 2.64(t, j=5.3 Hz, 2H), 2.13 (s, 3H), 1.99 (s, 3H).

Provenance & Evidence