Benzoyl chloride, 3-nitro- → (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)-methanone

Participants

Reaction Steps

n-BuLi (22 mL, 2.5 M in Hexane, 55.0 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (15.0 g, 50.0 mmol) in THF (200 mL) at −78° C. After 1 h the resulting solution was added via cannula to a solution of 3-Nitrobenzoyl Chloride in THF (100 mL) at −78° C. After 30 min the reaction was quenched with saturated aqueous NH4Cl and warmed to room temperature. The layers were separated and the aqueous layer was extracted with EtOAc (1×200 mL). The THF was concentrated off under reduced pressure and the resulting organic layer was diluted with EtOAc. The organic layer was washed with 1N NaOH (2×) and water (1×) then dried over Na2SO4 and concentrated. Recrystallization from EtOAc afforded the title compound as a white solid (12.1 g, 65%). MS: 371.2/373.1 (MH+); HPLC Rf: 6.59 min. (HPLC method 4).

Provenance & Evidence