Lithium hydroxide, monohydrate → 3-(3-hydroxypropyl)-5-isopentyl-6-isopropoxy-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

To a solution of 3-(5-isopentyl-6-isopropoxy-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (48 mg, 0.123 mmol) in THF (1 mL) and water (1 mL) was added LiOH.H2O (10.3 mg, 0.246 mmol). The reaction was stirred at RT for 15 min then diluted with EA (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 3-(3-hydroxypropyl)-5-isopentyl-6-isopropoxy-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (22.6 mg, 50.5% yield) as a white solid. 1H NMR (CDCl3) δ: 8.24 (s, 1H), 4.61-4.56 (m, 1H), 4.32-4.13 (m, 2H), 3.68 (s, 3H), 3.55 (d, J=5.3 Hz, 2H), 3.32 (dd, J=17.2, 9.1 Hz, 3H), 2.02-1.84 (m, 2H), 1.71 (dd, J=13.2, 6.6 Hz, 1H), 1.39 (d, J=6.0 Hz, 6H), 0.99 (d, J=6.6 Hz, 6H). LCMS: MH+ 364 and TR=3.032 min.

Provenance & Evidence