Abstract
A new method is presented for the synthesis of 2-aminoquinazolines, which is based on a Chan–Evans–Lam coupling of (2-formylphenyl)boronic acids with guanidines. Relatively mild conditions involving the use of inexpensive CuI as a catalyst and methanol as a solvent permit the application of the method to a wide range of substrates. Nonsubstituted, N-monosubstituted, and N,N-disubstituted guanidines can be used as reactants to give the corresponding 2-aminoquinazolines in moderate yields from readily available (2-formylphenyl)boronic acids.
Highlights
The only precedent for accessing quinazoline derivatives by using Chan–Evans–Lam coupling is a synthesis of quinazolonimines by arylation of N,Ndisubstituted guanidines, formed in situ, with (2-cyanophenyl)boronic acids.[25]
To facilitate our kinase-inhibitordevelopment program, we examined whether the Chan– Evans–Lam coupling might be applicable to the synthesis of aminoquinazolines under mild conditions by using readily available reagents
A screening of the reaction conditions was performed for the synthesis of unsubstituted quinazoline-2-amine (3)
Summary
A screening of the reaction conditions was performed for the synthesis of unsubstituted quinazoline-2-amine (3). Chan–Evans–Lam coupling, quinazolines, copper catalysis, formylphenylboronic acids The only precedent for accessing quinazoline derivatives by using Chan–Evans–Lam coupling is a synthesis of quinazolonimines by arylation of N,Ndisubstituted guanidines, formed in situ, with (2-cyanophenyl)boronic acids.[25] To facilitate our kinase-inhibitordevelopment program, we examined whether the Chan– Evans–Lam coupling might be applicable to the synthesis of aminoquinazolines under mild conditions by using readily available reagents.
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