5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)-6-(3-(trifluoromethoxy)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione → 5-(1-hydroxy-3-methylbutyl)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (60 mg, 0.104 mmol) was dissolved in 2N HCl/MeOH (5 mL). The reaction was stirred at RT for 1 h then diluted with EA (10 mL) and water (10 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(1-hydroxy-3-methylbutyl)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (20 mg, 38.5% yield) as a white solid. 1H NMR (DMSO-d6) δ: 8.59 (s, 1H), 7.48 (t, J=8.4 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 6.98-6.92 (m, 3H), 5.62-5.60 (m, 2H), 4.54 (t, J=5.2 Hz, 1H), 4.06-4.01 (m, 2H), 3.60 (s, 3H), 3.46-3.52 (m, 2H), 1.92-1.90 (m, 1H), 1.80-1.72 (m, 3H), 1.24-1.19 (m, 1H), 0.83 (d, J=6.8 Hz, 3H), 0.75 (d, J=6.8 Hz, 3H). LCMS: MH+ 498 and TR=3.186 min.

Provenance & Evidence