Sodium Carbonate → 5-(4-chlorobenzyl)-6-(3-fluorophenyl)-3-(3-hydroxy propyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(6-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (70 mg, 0.15 mmol), 3-fluorophenylboronic acid (31 mg, 0.22 mmol), Na2CO3(0.6 ml) in THF (3.2 mL) and EtOH (1.6 mL) was added Pd(PPh3)4 (25 mg, 0.015 mmol). The reaction was heated at 100° C. for 18 h, cooled to RT then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4, and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-(3-fluorophenyl)-3-(3-hydroxy propyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (50 mg, 85% yield) as white solid. 1H NMR (CDCl3) δ: 8.53 (s, 1H), 7.36 (dd, J=8.0, 6.0 Hz, 1H), 7.19-7.06 (m, 3H), 6.97-6.86 (m, 2H), 6.77 (d, J=8.3 Hz, 2H), 4.63 (s, 2H), 4.19 (t, J=6.1 Hz, 2H), 3.78 (s, 3H), 3.47 (dd, J=11.7, 6.1 Hz, 2H), 2.92 (t, J=6.9 Hz, 1H), 1.96-1.77 (m, 2H). LCMS: MH+ 454 and TR=3.00 min.

Provenance & Evidence