Water → HCID 58961526, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.47 g, 6.38 mmol) in THF (60 mL) at −78° C. under N2 was added n-BuLi (2.5 M in hexane, 5.74 mL, 14.36 mmol) dropwise. After completion of addition, the mixture was stirred at −78° C. for additional 40 min. PhCOCl (0.88 mL) was added and the reaction was stirred for an additional 1 hour. Water (1 mL) was added to quench the reaction. The reaction mixture was then poured into water (100 mL). EtOAc (200 mL) was added for extraction. The organic layer was separated, dried (Na2SO4), filtered and concentrated to a residue. The residue was dissolved into small amount of DCM and a little MeOH. It was loaded to silica gel column. The purification was down by eluent with 1/1 DCM/EtOAc. The (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(phenyl)methanone was obtained as a white solid (0.49 g, 29%). 1H NMR (DMSO-d6, 400 MHz) 8.74 (s, 1H), 8.17 (s, 1H), 7.87 (m, 2H), 7.68 (m, 1H), 7.56 (m, 2H). LCMS [M+1]: 258.

Provenance & Evidence