Potassium Carbonate → 7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-((5-methylpyridin-3-yl)oxy)-1H-purine-2,6(3H,7H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-chloro-7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (30 mg, 0.08 mmol, intermediate 78) in DMF (2 mL) was added 5-methylpyridin-3-ol (12.36 mg, 0.12 mmol), followed by potassium carbonate (15.66 mg, 0.11 mmol). The reaction was stirred at 80° C. for 3 h. The reaction was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, and concentrated to give a crude product, which was purified by preparative HPLC to give 7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-((5-methylpyridin-3-yl)oxy)-1H-purine-2,6(3H,7H)-dione (8 mg, 22.5%) as white solid. 1H-NMR (CD3OD) δ 8.35-8.42(d, 2H), 7.68(s, 1H), 7.38-7.48(m, 4H), 5.52(s, 2H), 4.01-4.14(m, 4H), 3.61-3.64(m, 2H), 2.43(s, 3H), 1.87-1.90(m, 2H), 1.22-1.26(m, 3H). LCMS retention time 2.511 min; LCMS MH+ 470.

Provenance & Evidence