Acetyl chloride → HCID 90403050, compound

Participants

Reaction Steps

To a solution of 7-((5-chloropyridin-2-yl)methyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(2-(3-(trifluoromethoxy)phenoxy)ethoxy)-1H-purine-2,6(3H,7H)-dione (80 mg, 0.14 mmol) in ethanol (5 mL) was added acetyl chloride (0.2 mL) at 0° C. The mixture was stirred at room temperature for 1 h. The mixture was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate, filtered and concentrated to give crude product which was purified by preparative HPLC to give 7-((5-chloropyridin-2-yl)methyl)-1-(3-hydroxypropyl)-3-methyl-8-(2-(3-(trifluoromethoxy)phenoxy)ethoxy)-1H-purine-2,6(3H,7H)-dione (15 mg, 19.0% yield) as white solid. 1H-NMR (CD3OD) δ 8.33(d, 1H), 7.70(dd, 1H), 7.35(t, 1H), 7.26(d, 1H), 6.87(dd, 1H), 6.76(s, 1H), 5.43(s, 2H), 4.86-4.87(m, 2H), 4.33-4.35(m, 2H), 4.04(t, 2H), 3.56(t, 2H), 3.54(s, 3H), 1.80-1.85(m, 2H). LCMS retention time 2.606 min; LCMS MH+ 570.

Provenance & Evidence