Acetic Acid → 6-Chloro-2,3-dihydro-3-hydroxy-2-imino-4-pyrimidinamine

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.C(O)(=[O:12])C.OO>O1CCCC1>[NH2:9][C:4]1[N:3]([OH:12])[C:2](=[NH:1])[N:7]=[C:6]([Cl:8])[CH:5]=1

Participants

Procedure

1.5 g (10 mmoles) of 2,6-diamino-4-chloropyrimidine are dissolved in 20 ml of anhydrous tetrahydrofuran. A mixture of 10 ml of acetic acid and 2 ml of a 70% aqueous hydrogen peroxide solution is added in 30 minutes under stirring and reflux. The reaction mixture is boiled for four hours, evaporated in vacuo to third of its volume, and a 40% aqueous sodium hydroxide solution is added to the residue until reaching a pH value of 8. The mixture is allowed to stand in refrigerator for a night. The crystals are filtered, washed with water and dried. In this way 1.0 g (63%) of the aimed compound is obtained.