Nitrogen → 2,4-dichloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine(2.2 g, 21.9 mmol, 1.5 eq) in THF (50 mL) was added nBuLi (2.5 mol/L, 6.4 mL, 16.07 mmol, 1.1 eq) dropwise under N2 at −78° C., then the mixture was stirred for 30 min at −78° C. And followed by 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (5 g, 14.6 mmol, 1 eq) in THF (50 mL) was added to the mixture, then the mixture was stirred for another 30 min at −78° C. Mel (2.28 g, 16 mmol, 1.1 eq) was added to the mixture for 30min at −78° C. The mixture was stirred at room temperature overnight and quenched with sat NH4Cl, then extracted with EtOAc. The organic layer was dried over Na2SO4, and the solvent was removed under reduced pressure to give the crude product which was purified by reverse phase preparative HPLC to afford 2.5 g of 2,4-dichloro-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine as a white solid. ESIMS (M+H)+=358.

Provenance & Evidence