N,N'-Dimethylethylenediamine → HCID 121249607, compound

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 (0.025 g, 0.097 mmol), 1-iodo-3-tertbutyl benzene (0.20 g, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (0.005 g, 0.049 mmol), Copper Iodide (0.004 g, 0.020 mmol), and Potassium Phosphate (0.041 g, 0.194 mmol) in 0.5 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 3×'s with EtOAc (˜5 mL) and 2×'s with NaHCO3 (˜10 mL). The crude organic layers were combined, dried over anhydrous Na2SO4 (s), filtered and the concentrated in vacuo. The crude mixture was then purified using the ISCO flash chromatography system using an 0-100% EtOAc gradient/100-0% Hexane gradient mixture. After concentrating the appropriate fractions, the pure product was collected as an off white solid (5 mg, 19%). 1H NMR (DMSO) δ: 7.94 (s, 1H), 7.46-7.55 (m, 2H), 7.47 (m, 1H), 7.28-7.36 (m, 2H), 6.32 (s, 2H), 6.21 (m, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 2.66(t, j=5.3 Hz, 2H), 2.25 (s, 3H), 2.09 (s, 9H).

Provenance & Evidence