Lithium hydroxide, monohydrate → HCID 118863125, compound

Participants

Reaction Steps

To a solution of 3-(5-(4-chlorobenzyl)-6-(3-chlorophenoxy)-1-methyl-2,4-dioxo-1,2-dihydro thieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetate (40 mg, 0.068 mmol) in THF (3 mL) and water (3 mL) was added LiOH.H2O (8.6 mg, 0.20 mmol). The reaction was stirred at RT for 15 min then diluted with EA (20 mL) and water (20 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-chlorophenoxy)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (13 mg, 38.9% yield) as a white solid. 1H NMR (CDCl3) δ: 7.26-7.24 (m, 2H), 7.23 (d, J=6.0 Hz, 2H), 7.20 (s, 3H), 7.16 (d, J=8.5 Hz, 4H), 7.11 (d, J=8.0 Hz, 2H), 6.93 (dd, J=19.3, 5.2 Hz, 4H), 4.18 (dd, J=14.0, 8.0 Hz, 9H), 3.60-3.44 (m, 1H), 3.23 (t, J=7.1 Hz, 2H), 1.96-1.85 (m, 4H). LCMS: MH+ 491 and TR=3.276 min.

Provenance & Evidence