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

Participants

Reaction Steps

To a solution of 5-(4-chlorobenzyl)-6-(3-fluorophenyl)-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (25 mg, 0.06 mmol) in MeOH (1 mL) was added 10% Pd/C (10 mg). The reaction was hydrogenated (15 psi) at 70° C. for 1 h, cooled to RT then diluted with EA (30 mL) and water (30 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-benzyl-6-(3-fluorophenyl)-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (10 mg, 43.5% yield) as a solid. 1H NMR (CDCl3) δ: 8.52 (s, 1H), 7.35 (d, J=8.0, 6.0 Hz, 1H), 7.23-7.06 (m, 4H), 6.98 (t, J=8.0 Hz, 1H), 6.93-6.87 (m, 1H), 6.84 (d, J=6.9 Hz, 2H), 4.68 (s, 2H), 4.17 (dd, J=20.0, 13.9 Hz, 2H), 3.77 (s, 3H), 3.42 (t, J=5.2 Hz, 2H), 2.89 (s, 1H), 1.91-1.80 (m, 2H). LCMS: MH+ 420 and TR=2.83 min.

Provenance & Evidence