Potassium Carbonate → HCID 90402592, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (80 mg, 0.17 mmol, intermediate 9) in DMF (5 mL) was added (1-(hydroxymethyl)cyclopropyl)methyl methanesulfonate (0.1 g, 0.5 mmol, intermediate 42), potassium carbonate (47 mg, 0.34 mmol) and TBAI (2 mg, 0.02 mmol). The reaction was stirred at 50° C. for 8 h. The mixture was cooled and partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by preparative HPLC to give 7-(4-chlorobenzyl)-1-((1-(hydroxymethyl)cyclopropyl)methyl)-3-methyl-8-(3(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (36 mg, 39.9% yield) as a white solid. 1H-NMR (CD3OD) δ 7.39(t, 1H), 7.01(dd, 1 H), 6.88-6.90(m, 2H), 4.87-4.88(m, 2H), 4.44-4.46(m, 2H), 4.08-4.16(m, 4H), 3.61(t, 2H), 3.51(s, 3H), 1.80-1.90(m, 2H), 1.32(t, 3H). LCMS retention time 3.099 min; LCMS MH+ 533.

Provenance & Evidence