Isocytosine synthesis
- Product Name:Isocytosine
- CAS Number:108-53-2
- Molecular formula:C4H5N3O
- Molecular Weight:111.1
Yield:-
Reaction Conditions:
with sodium chloride;sodium ethanolate in water
Steps:
I.a Isocytosine from 1,3-Dimethyluracil
(a) Guanidine hydrochloride (IIIc) (10 g, 0.1 mol) was added to 1 M sodium ethoxide (100 ml) and the mixture was stirred for 10 minutes at room temperature after which the mixture was filtered quickly from sodium chloride. To the filtrate was added 1,3-dimethyluracil (1.4 g, 0.01 mol) and the mixture refluxed for 18 hours under nitrogen. The solvent was removed by evaporation under reduced pressure and the syrupy residue dissolved in water (30 ml). The solution was passed through a column of Amberlite IRC-50 (H+) and the column washed with water. The uv absorbing fractions were combined and evaporated in vacuo to dryness to a syrup which crystallized upon trituration with ethanol. The yield of isocytosine (IIIc, R1, R2 =H) was 0.73 g (66%), mp 265°-267°. A mixed melting point with an authentic sample of isocytosine was not depressed. The uv and ir spectrum of the product was identical with that for isocytosine. In accordance with the above procedure but where, in place of 1,3-dimethyluracil, there is employed 1,3-diethyluracil, 1,3-ditertbutyluracil or 1,3-dibenzyluracil there is obtained the same product.
References:
Research Corporation US4171429, 1979, A
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