Guanidine Hydrochloride → 5-Amino-3H-thiazolo[4,5]pyrimidine-2-one

Participants

Reaction Conditions

Reaction Steps

Compound 85 (1.22 g, 7.47 mmol), guanidine hydrochloride (2.13 g, 22.4 mmol), K2CO3 (1.03 g, 7.47 mmol), and NaHCO3 (1.88 g, 22.3 mmol) was suspended in DMF and heated for two days at 110° C. Upon consumption of the starting material as determined by TLC, the solvent was removed under vacuurn. The solid residue was triturated with water. An analytically pure sample of 86 was obtained by HPLC (ODS-A C18; 3-97% CH3CN/H2O gradient; 1.0 mL/min). Tan solid: HPLC Rt=1.63 min; Rf=0.45 (2% H2O, 8% Methanol, 90% Ethyl acetate); 1H NMR (400 MHz, d6-DMSO) δ 8.11 (s, 1H), 6.67 (s, 2H); MS (+)-ES [M+H]+ 169; Elemental analysis for C5H4N4OS.0.1 CH3CN.0.1 H2O: calc'd: C, 35.88; H, 2.61; N, 32.99; S, 18.42. Found: C, 35.96; H, 2.75; N, 32.56; S, 18.42.

Provenance & Evidence