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

Temperature

-78 °C

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.

1. additionwas added to the mixture
2. stirringthe mixture was stirred for another 30 min at −78° C
3. additionMel (2.28 g, 16 mmol, 1.1 eq) was added to the mixture for 30min at −78° C
4. stirringThe mixture was stirred at room temperature overnight
5. customquenched with sat NH4Cl
6. extractionextracted with EtOAc
7. dry with materialThe organic layer was dried over Na2SO4
8. customthe solvent was removed under reduced pressure
9. customto give the crude product which
10. customwas purified by reverse phase preparative HPLC

ORD record

ord-55584abd652a4009ab04d188f1211bc0

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07981903B2