A suitably substituted pyrimidine 1 was converted to a number of title compounds. Nucleophilic substitution involving the chlorine atoms in 1 by treatment with phenylmethanethiol yielded 2 or 3, depending on the reaction temperature. Treatment of 3 with an amine afforded 6-​phenylmethanesulfanyl-​N4-​substituted-​2-​phenyl-​pyrimidine-​4,5-​diamines 4-​7. These pyrimidines were converted into 2-​phenylpurines 8-​11 and 2-​phenyl-​8-​azapurines 12-​14, by treatment with triethyl orthoformate in the presence of hydrochloric acid (or acetic anhydride), or with potassium nitrite and acetic acid respectively. The thioether function on C(6) was then converted into a sulfonyl group by oxidation with m-​chloroperoxybenzoic acid affording purines 15-​18 and their 8-​azaanalogs 19-​21; these compounds, as crude products, were treated with an amine to yield the corresponding adenines 22-​25 or 8-​azaadenines 26-​31. All reactions were performed under conditions compatible with the possible use of a thiomethyl resin in place of phenylmethanethiol to bind the pyrimidine ring of 1 to a solid phase.

Preparation of New N6,9-disubstituted-2-phenyladenines and corresèponding 8-azaadenines. A feasibility study for application to solid-phase synthesis

GIORGI, IRENE;
2004-01-01

Abstract

A suitably substituted pyrimidine 1 was converted to a number of title compounds. Nucleophilic substitution involving the chlorine atoms in 1 by treatment with phenylmethanethiol yielded 2 or 3, depending on the reaction temperature. Treatment of 3 with an amine afforded 6-​phenylmethanesulfanyl-​N4-​substituted-​2-​phenyl-​pyrimidine-​4,5-​diamines 4-​7. These pyrimidines were converted into 2-​phenylpurines 8-​11 and 2-​phenyl-​8-​azapurines 12-​14, by treatment with triethyl orthoformate in the presence of hydrochloric acid (or acetic anhydride), or with potassium nitrite and acetic acid respectively. The thioether function on C(6) was then converted into a sulfonyl group by oxidation with m-​chloroperoxybenzoic acid affording purines 15-​18 and their 8-​azaanalogs 19-​21; these compounds, as crude products, were treated with an amine to yield the corresponding adenines 22-​25 or 8-​azaadenines 26-​31. All reactions were performed under conditions compatible with the possible use of a thiomethyl resin in place of phenylmethanethiol to bind the pyrimidine ring of 1 to a solid phase.
2004
Biagi, G; Giorgi, Irene; O., Livi; F., Pacchini; V., Scartoni; O., LEROY SALERNI
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/206315
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