Acetic Anhydride → HCID 90403408, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-(4-chlorobenzyl)-1-(2-hydroxy-3-methoxypropyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (40 mg, 0.072 mmol, example 7f) in methyl sulfoxide (4 mL) was added acetic anhydride (37 mg, 0.363 mmol) dropwise. Then the mixture was stirred at 25° C. for 16 h. The mixture was partitioned between ethyl acetate and water and the organic phase was washed with brine, dried over sodium sulfate, filtered and was concentrated to give crude product. This crude material was further purified preparative HPLC to give 7-(4-chlorobenzyl)-1-(3-methoxy-2-oxopropyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (12 mg, 30.2%) as white solid. 1H-NMR (CD3OD) δ 7.56-7.52(t, 1H), 7.42-7.39(d, 2H), 7.36-7.31(m, 4H), 7.24-7.22(d, 1H), 5.45(s, 2H), 4.92(s, 2H), 4.24(s, 2H), 3.46(s, 3H), 3.39(s, 3H). LCMS retention time 3.210 min; LCMS MH+ 553.

Provenance & Evidence