Lithium hydroxide, monohydrate → 3-(3-hydroxypropyl)-1-methyl-5-(4-(trifluoromethyl)benzyl)-6-(3-(trifluoromethyl)phenoxy)pyrido[2,3-d]pyrimidine-2,4 (1H,3H)-dione

Participants

Reaction Steps

To a solution of 3-(1-methyl-2,4-dioxo-5-(4-(trifluoromethyl)benzyl)-6-(3-(trifluoromethyl) phenoxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (150 mg, 0.258 mmol) in THF (2 mL) was added aq. LiOH.H2O (1 mL, 0.5 M). The reaction was stirred at RT for 10 min then extracted with EA (50 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 3-(3-hydroxypropyl)-1-methyl-5-(4-(trifluoromethyl)benzyl)-6-(3-(trifluoromethyl)phenoxy)pyrido[2,3-d]pyrimidine-2,4 (1H,3H)-dione (20 mg, 8% yield over 3 steps) as a white solid. 1H NMR (CDCl3) δ: 8.37 (s, 1H), 7.42 (m, 3H), 7.35 (m, 1H), 7.31 (m, 2H), 7.02 (m, 2H), 4.83 (s, 2H), 4.24 (t, J=6.1 Hz, 2H), 3.73 (s, 3H), 3.56 (s, 2H), 2.95 (s, 1H), 1.98-1.87 (m, 2H). LCMS: MH+ 554 and TR=3.39 min.

Provenance & Evidence