Palladium-Catalyzed Animation of 6-Chloropurine. Synthesis of N⁶-Substituted Adenosine Analogues

References

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• Isolated yields. Typical procedure: To a solution of chloropurine 7 (1 mmole), coevaporated twice with toluene (2 mL), in freshly distilled THF (5 mL) was added consecutively the indicated amine (2 mmole), base (1.5 mmole), BINAP (0.025 mmole) and Pd2(dba)3, (0.01 mmole). After stirring the indicated time at room temperature under a nitrogen atmosphere, the reaction was quenched by the addition of a saturated solution of NH4Cl and extracted with EtOAc. The organic phase was washed with H2O and brine, dried with MgSO4, and filtered before concentration and purification by silica gel column chromatography (eluent: EtOAc/PE 60–80).
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• All compounds showed satisfactory analytical and spectroscopic data. TBS = tert-butyldimethylsilyl, Bn = benzyl, Pd(dba)2, = bis(dibenzylideneacetone)palladium, BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl.
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• Transition-metal catalysis has also been applied in the condensation of 6-halopurines with Grignard,15, organotin24,25, and organozinc26, reagents.
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