1027381-72-1

Upstream product

• 778594-77-7 N⁴-(p-methoxyphenylmethyl)-2-phenylpyrimidine-6-phenylmethanesulfanyl-4,5-diamine 
• 20959-02-8 5-amino-4,6-dichloro-2-phenylpyrimidine 
• 2393-23-9 4-methoxy-benzylamine 
• 778594-84-6 9-(p-methoxyphenylmethyl)-2-phenyl-6-phenylmethanesulfanyl-8-azapurine 
• 778594-73-3 5-amino-4-chloro-2-phenyl-6-phenylmethanesulfanylpyrimidine 
• 100-53-8 phenylmethanethiol 

Relevant academic research and scientific papers

Preparation of new N6,9-disubstituted 12-phenyl-adenines and corresponding 8-azaadenines. A feasibility study for application to solid-phase synthesis. I [1]

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 tniomethyl resin in place of phenylmethanethiol to bind the pyrimidine ring of 1 to a solid phase.