Dimethylformamide → 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde

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Reaction Conditions

Reaction Steps

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2.33 g, 10.0 mmol, 1.0 eq) in anhydrous THF (100 mL) at −78° C. under argon, n-BuLi solution (2.5 M in THF, 8.8 mL, 22.0 mmol, 2.2 eq) was added dropwise (over 10 min). The resulting mixture was stirred at −78° C. for 1 h and then DMF (2.0 g, 11.0 mmol, 1.1 eq) was added dropwise (over 10 min). The mixture was stirred at −78° C. for an additional 30 min and then stirred at RT overnight. The reaction mixture was quenched with H2O (50 mL) and then concentrated in vacuo. The residue was triturated with saturated aqueous NH4Cl solution. The solid was collected by filtration, rinsed with ethyl acetate, and dried in vacuo to afford 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (1.17 g, 65% yield).

Provenance & Evidence