Potassium Carbonate → HCID 90402383, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-hydroxybutyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)— dione (50 mg, 0.121 mmol, intermediate 57) in DMF (3 mL) was added 2-(chloromethyl)-5-methylpyridine hydrochloride (30 mg, 0.182 mmol, intermediate 50), followed by potassium carbonate (50 mg, 0.363 mmol) and TBAI (10 mg, 0.027 mmol). The reaction was stirred at 65° C. overnight. The reaction was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product, which was purified by preparative HPLC to give 1-(3-hydroxybutyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (20 mg, 31.9% yield) as white solid. 1H-NMR (CD3OD) δ 8.319(s,1H), 7.663-7.640(d,1H), 7.553-7.510(t,1H), 7.348-7.316(m,3H), 7.233-7.208(m,1H), 5.609(s, 2H), 4.112-4.004(m,2H), 3.763-3.731(m,1H), 3.457(s,3H), 2.339(s,3H), 1.758-1.698(m,2H), 1.197-1.182(d,2H). LCMS retention time 2.714 min; LCMS MH+ 520.

Provenance & Evidence