Lithium hydroxide, monohydrate → HCID 118863146, compound

Participants

Reaction Steps

To a solution of 3-(5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetate (40 mg, 0.070 mmol) in THF (4 mL) and water (4 mL) was added LiOH.H2O (5.88 mg, 0.14 mmol). The reaction was stirred at RT for 15 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)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (16 mg, 48.1% yield) as a white solid. 1H-NMR (DMSO-d6) δ: 7.49 (d, J=5.1 Hz, 2H), 7.40 (s, 1H), 7.36-7.32 (m, 1H), 7.29 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.4 Hz, 2H), 4.45 (t, J=5.2 Hz, 1H), 4.30 (s, 2H), 3.97-3.82 (m, 2H), 3.52 (d, J=14.8 Hz, 3H), 3.42 (dd, J=11.7, 6.3 Hz, 2H), 1.67 (dd, J=14.2, 6.9 Hz, 2H). LCMS: MH+ 475 and TR=3.252 min.

Provenance & Evidence