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

Temperature

-78 °C

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).

1. stirringThe mixture was stirred at −78° C. for an additional 30 min
2. stirringstirred at RT overnight
3. customThe reaction mixture was quenched with H2O (50 mL)
4. concentrationconcentrated in vacuo
5. customThe residue was triturated with saturated aqueous NH4Cl solution
6. filtrationThe solid was collected by filtration
7. washrinsed with ethyl acetate
8. customdried in vacuo

ORD record

ord-f48b0753ae664f3ab9d90fc2b28b9892

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969363B2