Hydrogen Peroxide → 1-Acetoxy-6-amino-1,2-dihydro-2-imino-4-(4-toluenesulfonyloxy)pyrimidine

HRID 868639

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([O:8][S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[C:4]([NH2:19])[N:3]=1.OO.[C:22]([O:25]C(=O)C)(=[O:24])[CH3:23]>C(O)C>[NH2:19][C:4]1[N:3]([O:25][C:22](=[O:24])[CH3:23])[C:2](=[NH:1])[N:7]=[C:6]([O:8][S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2.8 g (0.001 mole) of 2,6-diamino-4-tosyloxypyrimidine are added to 70 ml of absolute ethanol. 5 ml of a 70% aqueous hydrogen peroxide solution are added to the obtained suspension at 40° C., then 3 ml of acetic anhydride are added dropwise. The suspension is homogenised by heating to 60° C., and the solution gets slowly opalescent while standing. Tracing the reaction by thin layer chromatography it will be found that the reaction has completed and the aimed compound is accompanied by some diacetyl compound. By filtering the reaction mixture 0.35 g of a solid material is separated. If the ethyl alcohol is distilled off and the residue is allowed to stand in a refrigerator, no product separation can be observed. Of decanting the water and dissolving the residue in ethanol a crystalline product is obtained. In this way 1.95 g (54%) of the aimed compound are obtained.

Workup

customthe reaction by thin layer chromatography it

Sources & evidence

ORD record: ord-ee61d2b4999d42c59e3023196be5d79d
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04780537

Linked notes

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