Oxidative amination of cuprated pyrimidine and purine derivatives.
Using regioselective cuprations (via magnesiations), various primary, secondary and tertiary aminated pyrimidine and purine derivatives were prepared by the oxidative coupling of lithium amidocuprates using chloranil. DNA and RNA units such as aminated uracil or thymine, and adenine, as well as a CDK inhibitor, purvalanol A, were all obtained under mild conditions and satisfactory yields.
Boudet
Nadège
N
Department Chemie and Biochemie, Ludwig-Maximilians-Universität, München, Germany.
Dubbaka
Srinivas Reddy
SR
Knochel
Paul
P
D000225:Adenine / Q000031:analogs & derivatives; D000586:Amination; D003300:Copper / Q000737:chemistry; D010084:Oxidation-Reduction; D011687:Purines / Q000138:chemical synthesis / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013941:Thymine / Q000031:analogs & derivatives; D014498:Uracil / Q000031:analogs & derivatives
C471843:6-((3-chloro)anilino)-2-(isopropyl-2-hydroxyethylamino)-9-isopropylpurine; D011687:Purines; D011743:Pyrimidines; D014498:Uracil; D003300:Copper; D000225:Adenine; D013941:Thymine; C029892:cupric chloride