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

Participants

Reaction Steps

To a solution of 3-(5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (40 mg, 0.08 mmol) in THF (1.5 mL) and water (1.5 mL) was added LiOH.H2O (30.0 mg, 0.6 mmol). The reaction was stirred at RT for 30 min 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)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (3 mg, 3.3% yield) as a white solid. 1H NMR (CDCl3) δ: 7.47-7.31 (m, 3H), 7.24-7.15 (m, 3H), 6.84 (d, J=8.4 Hz, 2H), 6.08 (s, 1H), 5.58 (s, 2H), 4.26-4.14 (m, 2H), 3.60 (s, 1H), 3.51 (s, 5H), 1.93-1.82 (m, 2H). LCMS: MH+ 458 and TR=2.885 min.

Provenance & Evidence