4-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), 4-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 (40 mg, 0.191 mmol) in 0.5 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (15 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 an 0-100% gradient EtOAc/100-0% gradient Hexane. Following concentration of the appropriate fractions in vacuo the product was further purified by recrystallization using a Et2O/Hexane solvent mixture to give the title compound as a light grey solid (15 mg, 39%). 1H NMR (DMSO) δ: 7.90 (s, 1H), 7.46-7.53 (m, 2H), 7.43 (d, J=6.7 Hz, 1H), 7.22-7.30 (m, 2H), 6.28 (s, 2H), 6.17 (d, J=7.0 Hz, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 3.02 (s, 6H) 2.65(t, j=5.3 Hz, 2H), 2.17 (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 was 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), 4-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 (40 mg, 0.191 mmol) in 0.5 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (15 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 an 0-100% gradient EtOAc/100-0% gradient Hexane. Following concentration of the appropriate fractions in vacuo the product was further purified by recrystallization using a Et2O/Hexane solvent mixture to give the title compound as a light grey solid (15 mg, 39%). 1H NMR (DMSO) δ: 7.90 (s, 1H), 7.46-7.53 (m, 2H), 7.43 (d, J=6.7 Hz, 1H), 7.22-7.30 (m, 2H), 6.28 (s, 2H), 6.17 (d, J=7.0 Hz, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 3.02 (s, 6H) 2.65(t, j=5.3 Hz, 2H), 2.17 (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 was 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), 4-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 (40 mg, 0.191 mmol) in 0.5 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (15 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 an 0-100% gradient EtOAc/100-0% gradient Hexane. Following concentration of the appropriate fractions in vacuo the product was further purified by recrystallization using a Et2O/Hexane solvent mixture to give the title compound as a light grey solid (15 mg, 39%). 1H NMR (DMSO) δ: 7.90 (s, 1H), 7.46-7.53 (m, 2H), 7.43 (d, J=6.7 Hz, 1H), 7.22-7.30 (m, 2H), 6.28 (s, 2H), 6.17 (d, J=7.0 Hz, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 3.02 (s, 6H) 2.65(t, j=5.3 Hz, 2H), 2.17 (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 was further purified by recrystallization