Lithium hydroxide, monohydrate → HCID 118863780, compound

Participants

Reaction Steps

To a solution of 3-(5-(4-chlorobenzyl)-1,7-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (120 mg, 0.212 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (17.9 mg, 0.425 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)-1,7-dimethyl-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidine-2,4 (3H,5H)-dione (15 mg, 27% yield) as a white solid. 1H NMR (CDCl3) δ: 7.49 (t, J=8.0 Hz, 1H), 7.32 (d, J=8.3 Hz, 1H), 7.13 (dd, J=16.3, 8.0 Hz, 3H), 7.04 (s, 1H), 6.71 (d, J=8.4 Hz, 2H), 5.46 (s, 2H), 4.31-4.15 (m, 2H), 3.74 (s, 3H), 3.65 (s, 1H), 3.50 (s, 2H), 2.20 (s, 3H), 1.98-1.81 (m, 2H). LCMS: MH+ 522 and TR=3.111 min.

Provenance & Evidence