Hydrogen Peroxide → 7-Aminothiazolo[4,5-d]pyrimidin-2(3H)-one

Participants

Reaction Steps

To a suspension of 29 (770 mg, 4.2 mmol) in water (30 mL) was added 1N NaOH (4.2 mL) and 30% H2O2 (1.0 mL) and the reaction was stirred for 1 h at room temperature. Additional peroxide (2.0 mL) and hydroxide (5.0 mL) were added and the mixture was stirred for 1 h at 70° C. The reaction mixture was filtered and the filtrate was neutralized with glacial acetic acid. The resulting precipitate was filtered off while still hot, washed with cold water and dried to yield 0.52 g (74%): mp>370° C. UV λmax (pH 1) 267 nm (ε), 289 (): UV λmax (pH 7, 11) 285 nm (ε): 1H NMR (DMSO-d6) δ 7.18 (b, 2H, NH2, exchanges with D2O), 8.12 (s, 1H, C 5 H), 12.30 (b, 1H, N3H, exchanges with D2O). Anal. Calcd. for C5H4N4OS: C, 35.71: H, 2.40: N, 33.31: S, 19.07. Found: C, 35.50: H, 2.36: N, 33.13: S, 18.79.

Provenance & Evidence