Chemoselective high-throughput purification mediated by solid-supported reagents: its application to the first 6, 9-disubstituted purine library synthesis.
A new application of solid-supported reagents was developed to separate the alkylated N7/N9 regioisomers derived from commercially available 2-amino-6-chloropurine. Simple filtration through an alumina/H+ pad or scavenging by AG/Dowex-50W-X8 resin provides diverse N9 regioisomers selectively in moderate yields with high purities (>90%). This purification method can be conveniently used in a high-throughput format and facilitates the synthesis of a purine library without laborious regioisomer separation and aqueous work-up. The first library synthesis of 6,9-disubstituted purines is reported using the combination of this novel separation method in conjunction with polymer-supported reagents.
Kim
K
K
Hoffmann-La Roche, Inc., Roche Research Center, Nutley, NJ 07110, USA. kyungjin.kim@roche.com
McComas
W
W
D015075:2-Aminopurine / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D015394:Molecular Structure; D011108:Polymers; D011687:Purines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011108:Polymers; D011687:Purines; D015075:2-Aminopurine; C040510:2-amino-6-chloropurine