p-Toluenesulphonyl cyanide → HCID 178510331, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of anhydrous THF (40 ml) containing 5-Bromo-4-chloro-7H-pyrrolo[2,3-c]pyrimidine D3 (1 g) was added nBu-Li (2.5M, 5.2 ml, 12.9 mmol) dropwise at −78° C. under nitrogen. After this addition the resulting solution was stirred for 1 hour at −78° C. before adding 4-methylbenzenesulfonyl cyanide (935 mg, 5.2 mmol) and the resulting solution stirred for 1 hour at −78° C. and then allowed to warm up to room temperature overnight. The reaction was quenched with a saturated NH4Cl solution at 0° C., extracted with EtOAc (100 ml) and organic layer was washed with 5% NaHCO3 solution, dried Na2SO4, filtered and concentrated in vacuo to afford a yellow solid. Purified by flash chromatography on silica gel eluting with Pet Eth/EtOAc 1/2 to give the desired product D42 as a yellow solid in 350 mg. LCMS [MH+] 179.0 @1.17 min (5 min run)

Provenance & Evidence