Lithium hydroxide, monohydrate → 5-[(4-Chlorophenyl)methyl]-3-(3-hydroxypropyl)-1-methyl-6-[3-(trifluoromethoxy)phenyl]pyrrolo[3,2-d]pyrimidine-2,4-dione

Participants

Reaction Steps

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (30 mg, 0.054 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (4.58 mg, 0.109 mmol). The reaction was stirred at RT for 30 min then diluted with DCM (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-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidine-2,4 (3H,5H)-dione (4 mg, 14.4% yield) as a white solid. 1H NMR (CDCl3) δ: 7.47 (t, J=8.0 Hz, 1H), 7.31 (d, J=8.6 Hz, 1H), 7.26-7.24 (m, 1H), 7.20 (d, J=8.3 Hz, 3H), 6.81 (d, J=8.4 Hz, 2H), 6.10 (s, 1H), 5.59 (s, 2H), 4.26-4.13 (m, 2H), 3.56 (d, J=6.7 Hz, 1H), 3.50 (d, J=9.8 Hz, 5H), 1.90 (d, J=5.4 Hz, 2H). LCMS: MH+ 508 and TR=3.007 min.

Provenance & Evidence