5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine → HCID 86603158, compound

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Reaction Steps

n-BuLi (9.40 mL, 2.5 M in Hexane, 23.3 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (6.25 g, 22.2 mmol) in Et2O (190 mL) at −78° C. and stirred for 1 h. 2-(Benzhydrylidene-amino)-6,N-dimethoxy-N-methyl-isonicotinamide (10.0 g, 26.6 mmol) was added to the reaction mixture slowly and stirred for 3h, warmed to room temperature, and quenched with saturated aqueous NH4Cl (200 mL). The aqueous layer was extracted with EtOAc (3×200 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide a crude solid. Purification by flash column chromatography (ethyl acetate/hexanes 1:1) afforded the title compound as a yellow solid (7.31 mg, 63%). MS: 511.3 (MH+); HPLC Rf: 3.1 min. (HPLC method 3); HPLC purity: 100%.

Provenance & Evidence