Triethylamine → HCID 59643088, compound

Participants

Reaction Steps

To a solution of 7-(4-fluoro-phenyl)-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl chloride, 25, (1.02 g, 3.15 mmol) in CH2Cl2 (20 mL) is added N,O-dimethylhydroxylamine hydrochloride salt (0.37 g, 3.80 mmol) and triethylamine (1.32 mL, 9.50 mmol). The mixture is allowed to stir at room temperature for 16 hours. The reaction is diluted with H2O and extracted three times with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (5% to 40% EtOAc/hexanes) to afford 660 mg of the desired product: 1H NMR (300 MHz, CDCl3) δ 8.90 (s, 1H), 7.44 (dd, J=8.4, 5.9 Hz, 2H), 7.22 (dd, J=8.4, 5.9 Hz, 2H), 7.10 (s, 1H), 3.62 (s, 3H), 3.26 (s, 3H), 2.54 (s, 3H); ESI+ MS: m/z (rel intensity) 347.0 (100, M++H).

Provenance & Evidence