Hydrogen Peroxide → 2-(2-Hydroxy-3-chloropropyl)sulfinyl-5-chloropyrimidine

Participants

Reaction Steps

A solution of 35% H2O2 (1.7 mmol) and SeO2 (1.7 mmol) in water (2.5 ml) was added to a solution of 2-(2-hydroxy-3-chloropropyl)thio-5-chloropyrimidine (1.7 mmol) in methanol (10 ml). The mixture was stirred at room temperature for 18 h before saturated NaCl aq. (40 ml) was added and the mixture extracted with chloroform (3×20 ml). The dried (MgSO4) chloroform solution was evaporated and the residue crystallized from ethyl acetate; yield 59%; m.p. 170° C. 1H NMR (DMSO-d6): δ3.0-4.4 (6H, m), 9.10 (H-4, H-6). IR (KBr): 3400 (OH), 1060-1070 cm-1 (SO).

Provenance & Evidence