Pyridine → HCID 69557498, compound

Participants

Reaction Steps

To a solution of 187 mg (0.417 mmol) of [[2-(methylthio)-6-ethyl-7-([1,1′-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 5 mL of chloroform was added 0.11 mL of oxalyl chloride followed by 0.05 mL of pyridine. The mixture was stirred for 2 days then quenched into 4.0 mL of dilute ammonium hydroxide. The product was extracted into 5.0 mL of methylene chloride. The organic phase was dried with sodium sulfate and concentrated to 500 mg of yellow oil. The residue was purified by flash chromatography (5 g of silica, ethyl acetate) to provide 240 mg of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-([1,1′-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as an oil. nmr (300 MHz, CDCl3) δ0.82 (t, 3H), 2.52 (s, 3H), 2.59 (q, 2H), 3.77 (s, 3H), 5.00 (s, 2H), 5.40 (s, 2H), 5.68 (s, 1H), 6.54 (s, 1H), 6.85 (d, 1H), 7.1-7.6 (m, J=6.7, 8H)

Provenance & Evidence