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 (E-2) (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) is added dropwise (over 10 min). The resulting mixture is stirred at −78° C. for 1 h and then DMF (2.0 g, 11.0 mmol, 1.1 eq) is added dropwise (over 10 min). The mixture is stirred at −78° C. for an additional 30 min and then stirred at RT overnight. The reaction mixture is quenched with H2O (50 mL) and then concentrated in vacuo. The residue is triturated with saturated aqueous NH4Cl solution. The solid is collected by filtration, rinsed with ethyl acetate, and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (E-3).

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

ORD record

ord-a83455aca6fc4d6499d8a051de35a8bc

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181221B2