3-iodo-N,N-dimethylaniline

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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), 3-iodo-N,N-dimethylaniline (20 mg, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), copper iodide (5 mg, 0.020 mmol), and potassium phosphate (44 mg, 0.206 mmol) in 0.5 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (13 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 the concentrated in vacuo. The crude mixture was then purified using the ISCO flash chromatography system using a 0-100% EtOAc gradient/100-0% Hexane gradient. The fractions containing the product were concentrated in vacuo and then further purified by recrystallization using an Et2O/Hexane solvent mixture to give the title compound (13 mg, 37%). 1H NMR (DMSO) δ: 7.92 (s, 1H), 7.45-7.52 (m, 2H), 7.46 (m, 1H), 7.28-7.35 (m, 2H), 6.28 (s, 2H), 6.17 (m, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 3.00 (s, 6H), 2.66 (t, j=5.3 Hz, 2H), 2.18 (s, 3H). the reaction to cool to room temperature The reaction was extracted with EtOAc (3×5 mL) and with NaHCO3 (2×10 mL) dried over anhydrous Na2SO4 (s) filtered the concentrated in vacuo The crude mixture was then purified The fractions containing the product were concentrated in vacuo further purified by recrystallization

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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), 3-iodo-N,N-dimethylaniline (20 mg, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), copper iodide (5 mg, 0.020 mmol), and potassium phosphate (44 mg, 0.206 mmol) in 0.5 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (13 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 the concentrated in vacuo. The crude mixture was then purified using the ISCO flash chromatography system using a 0-100% EtOAc gradient/100-0% Hexane gradient. The fractions containing the product were concentrated in vacuo and then further purified by recrystallization using an Et2O/Hexane solvent mixture to give the title compound (13 mg, 37%). 1H NMR (DMSO) δ: 7.92 (s, 1H), 7.45-7.52 (m, 2H), 7.46 (m, 1H), 7.28-7.35 (m, 2H), 6.28 (s, 2H), 6.17 (m, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 3.00 (s, 6H), 2.66 (t, j=5.3 Hz, 2H), 2.18 (s, 3H). the reaction to cool to room temperature The reaction was extracted with EtOAc (3×5 mL) and with NaHCO3 (2×10 mL) dried over anhydrous Na2SO4 (s) filtered the concentrated in vacuo The crude mixture was then purified The fractions containing the product were concentrated in vacuo further purified by recrystallization