p-Toluenesulphonyl cyanide → HCID 178510331, compound

Temperature

-78 °C

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)

1. additionAfter this addition the resulting solution
2. stirringthe resulting solution stirred for 1 hour at −78° C.
3. temperatureto warm up to room temperature overnight
4. customThe reaction was quenched with a saturated NH4Cl solution at 0° C.
5. extractionextracted with EtOAc (100 ml) and organic layer
6. washwas washed with 5% NaHCO3 solution, dried Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto afford a yellow solid
10. customPurified by flash chromatography on silica gel eluting with Pet Eth/EtOAc 1/2

ORD record

ord-5bf544a1522c4850aafef4c01dee6c96

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045485B2