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

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Reaction Steps

To a solution of 3-(5-benzyl-6-isopropoxy-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (70 mg, 0.17 mmol) in THF (1 mL) and water (1 mL) was added LiOH.H2O (14.2 mg, 0.34 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 5-benzyl-3-(3-hydroxypropyl)-6-isopropoxy-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (18 mg, 39.0% yield) as a white solid. 1H NMR (CDCl3) δ: 8.32 (s, 1H), 7.25-7.18 (m, 4H), 7.17-7.10 (m, 1H), 4.78 (s, 2H), 4.62 (dt, J=12.1, 6.1 Hz, 1H), 4.26-4.15 (m, 2H), 3.69 (s, 3H), 3.52-3.43 (m, 2H), 3.17 (t, J=7.0 Hz, 1H), 1.94-1.82 (m, 2H), 1.34 (d, J=6.0 Hz, 6H). LCMS: MH+ 384 and TR=2.708 min.

Provenance & Evidence