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

Participants

Reaction Steps

To a solution of 3-(5-(4-chlorobenzyl)-6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydro pyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (35 mg, 0.069 mmol) in THF (6 mL) and water (6 mL) was added LiOH.H2O (5.8 mg, 0.138 mmol). The reaction was stirred for 15 min then diluted with EA (10 mL) and water (10 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-6-(2-isopropylphenyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (15 mg, 45.4% yield) as white solid, 1H NMR (DMSO-d6) δ: 8.49 (s, 1H), 7.40-7.38 (m, 2H), 7.18-7.14 (m, 3H), 6.93 (d, J=7.2 Hz, 1H), 6.75 (d, J=8.4 Hz, 2H), 4.68-4.65 (m, 1H), 4.45 (s, 1H), 4.24-4.20 (m, 1H), 3.95-3.91 (m, 2H), 3.64 (s, 3H), 3.42-3.40 (m, 2H), 2.40-2.36 (m, 1H), 1.70-1.66 (m, 2H), 1.01-1.00 (d, 3H), 0.85 (d, J=7.2 Hz, 3H). LCMS: [MH+—OH] 478 and TR=3.454 min.

Provenance & Evidence