Pyridine → HCID 69558654, compound

Participants

Reaction Steps

To a solution of 300 mg (0.770 mmol) of [[2-(methylthio)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 5 mL of chloroform was added 0.21 mL of oxalyl chloride followed by 0.09 mL of pyridine. The reaction was stirred for 2 days at ambient temperature then quenched into 4.0 mL of dilute ammonium hydroxide. The product was extracted into 4.0 mL of methylene chloride. The organic phase was washed with water, dried with sodium sulfate and concentrated to 430 mg of tan solid. The residue was purified by flash chromatography (45 g of silica, ethyl acetate) to provide 260 mg (73%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a solid. nmr (300 MHz, dmso-d6) δ1.00 (t, 3H), 2.45 (s, 3H), 2.90 (q, 2H), 3.65 (s, 3H), 4.97 (s, 2H), 5.52 (s, 2H), 6.91 (d, 1H), 7.03 (d, 1H), 7.12 (dt, 1H), 7.47 (dt, 1H), 7.60 (s, 1H), 8.01 (s, 1H)

Provenance & Evidence