Potassium Carbonate → 7-(4-chlorobenzyl)-1-(2-(1-hydroxycyclopropyl)ethyl)-3-methyl-8-((6-methylpyridin-3-yl)oxy)-1H-purine-2,6(3H,7H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-bromo-7-(4-chlorobenzyl)-1-(2-(1-hydroxycyclopropyl)ethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (128 mg, 0.282 mmol, intermediate 56) in DMF (5 mL) was added 6-methylpyridin-3-ol (37 mg, 0.338 mmol), followed by potassium carbonate (58 mg, 0.423 mmol). The reaction was stirred at 80° C. for 2 h. The reaction was 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 7-(4-chlorobenzyl)-1-(2-(1-hydroxycyclopropyl)ethyl)-3-methyl-8-((6-methylpyridin-3-yl)oxy)-1H-purine-2,6(3H,7H)-dione (110 mg, 80.9% yield) as white solid. 1H-NMR (CD3OD) δ 8.457-8.451(d,1H), 7.776-7.748(d,1H), 7.470-7.374(m, 5H), 5.519(s,2H), 4.291-4.256(t,2H), 3.411(s,3H), 2.584(s,3H), 1.867-1.832(t,2H), 0.618-0.610(m, 2H), 0.403-0.387(m,2H). LCMS retention time 2.619 min; LCMS MH+ 482.

Provenance & Evidence