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

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.
Biagi, G; Giorgi, Irene; O., Livi; F., Pacchini; V., Scartoni; O., LEROY SALERNI
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/206315
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 2
social impact