4-(7-Benzenesulfonyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester → 4-(7-Benzenesulfonyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

MeZnCl (2.0M in THF, 720 uL, 1.4 mmol) was added to a stirred solution 4-(7-Benzenesulfonyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (250 mg, 0.48 mmol) and tetrakis(triphenylphosphine)palladium(0) (140 mg, 0.12 mmol) in THF (10 mL) at room temperature under N2. The solution was stirred and heated at reflux for 2 hours, cooled to room temperature, quenched with saturated aqueous NH4Cl, extracted into EtOAc (2×100 mL), dried over Na2SO4 and concentrated in vacuo. The product was purified on a Biotage (silica, 40% EtOAc/hexanes) to give 4-(7-Benzenesulfonyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (210 mg, 94%.) LCMS (APCI+) m/z 458 [M+H]+; Rt: 3.73. 1H NMR (CDCl3, 400 MHz) δ 8.49 (1H, s), 8.18 (2H, d, J 8.2 Hz), 7.59 (1H, t, J 6.9 Hz), 7.50 (2H, t, J 7.8 Hz), 7.34 (1H, s), 3.59-3.54 (4H, m), 3.48-3.44 (4H, m), 2.35 (3H, s), 1.48 (9H, s.)

Provenance & Evidence