Pyridine → HCID 9801656, compound

Participants

Reaction Steps

To a solution of 715 mg (2.10 mmol) of [[2-methyl-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 15 mL of chloroform was added 0.55 mL of oxalyl chloride followed by 0.25 mL of pyridine. The reaction was stirred for 18 hours at ambient temperature then poured into a solution prepared from 1.7 mL of concentrated ammonium hydroxide and 5.8 mL of water. The reaction was partitioned by the addition of 15 mL of methylene chloride and a small amount of solid residue was removed by filtration. The organic phase was dried with sodium sulfate and concentrated to an off-white solid. The solid was purified by flash chromatography (100 g of silica, ethyl acetate) to provide 740 mg (86%) of [[2-methyl-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a white solid. nmr (500 MHz, CDCl3) δ1.10 (t, J=7.5 Hz, 3H), 2.59 (s, 3H), 2.91 (q, J=7.5 Hz, 2H), 3.76 (s, 3H), 5.04 (s, 2H), 5.50 (s, 2H), 6.25 (s, 1H), 6.66 (s, 1H), 7.13 (d, J=6.9 Hz, 2H), 7.28 (m, 3H)

Provenance & Evidence