N,N'-Dimethylethylenediamine → 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methyl-1-(m-tolyl)-1,6-dihydropyridin-2(3H)-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 (24 mg, 0.096 mmol), 1-iodo-3-methylbenzene (20 mg, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), copper iodide (5 mg, 0.022 mmol), and potassium phosphate (44 mg, 0.199 mmol) in 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 pale yellow solid (16 mg, 47%). 1H NMR (DMSO) δ: 7.99 (s, 1H), 7.80 (d, J=6.0, 1H), 6.56 (d, J=6.0, 1H), 6.28 (m, 1H), 6.20 (d, J=7.0 Hz, 2H), 3.99 (br. S, 2H), 3.31 (s, 2H), 2.66(t, j=5.3 Hz, 2H), 2.15 (s, 3H).

Provenance & Evidence