Pyridine → HCID 69558434, compound

Participants

Reaction Steps

To a solution of 831 mg (2.55 mmol) of [[6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 20 mL of chloroform was added 0.67 mL of oxalyl chloride followed by 0.30 mL of pyridine. The reaction was stirred for 18 hours at ambient temperature then poured into a solution prepared from 2.0 mL of concentrated ammonium hydroxide and 8.0 mL of water. The reaction was partitioned by the addition of 20 mL of methylene chloride and 10 mL of water. The organic phase was dried with sodium sulfate and concentrated. The residue was purified by flash chromatography (100 g of silica, ethyl acetate) to provide 420 mg (51%) of [[6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2, 3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 455 mg (45%) of [[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) δ1.13 (t, J=7.5 Hz, 3H), 2.95 (q, J=7.5 Hz, 2H), 3.77 (s, 3H), 5.06 (s, 2H), 5.53 (s, 2H), 6.28 (s, 1H), 6.70 (s, 1H), 7.13 (d, J=6.7 Hz, 2H), 7.27 (m, 3H), 8.46 (s, 1H)

Provenance & Evidence