p-Toluenesulphenyl cyanide → 4-Chloro-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile

To 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.31 g, 1.3 mmol) in dry THF (4 ml), cooled in a dry ice-acetone bath, was added dropwise n-butyllithium (1.3 ml, 3.3 mmol, 2.5 M In hexanes). The reaction mixture was stirred for 1 hour, then p-toluenesulphenyl cyanide (0.44 g, 2.4 mmol) suspended in dry THF (7 ml) was added. The solution was stirred for 18 hours at ambient temperature then diluted with aqueous ammonium chloride. The phases were separated and the organic phase washed with water and aqueous NaCl. The organic phase was dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel (15 g, 40 mm mesh) using 3% methanol/methylene chloride to afford 4-chloro5-cyano-7H-pyrrolo[2,3-d]pyrimidine as a yellow solid (52 mg).

1. additionwas added
2. stirringThe solution was stirred for 18 hours at ambient temperature
3. customThe phases were separated
4. washthe organic phase washed with water and aqueous NaCl
5. dry with materialThe organic phase was dried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by flash chromatography on silica gel (15 g, 40 mm mesh)

ORD-Eintrag

ord-504a4c7b292f438db9d77e6125064e41

Quelldatensatz

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06395733B1