Pyridine → HCID 69558786, compound

Participants

Reaction Steps

To a solution of 5.17 g (13.9 mmol) of [[2-(methylthio)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 100 mL of chloroform was added 3.64 mL of oxalyl chloride followed by 1.66 mL of pyridine. The reaction was stirred for 3 days at ambient temperature then poured into a solution prepared from 11 mL of concentrated ammonium hydroxide and 40 mL of water. The reaction was partitioned by the addition of 45 mL of water and 150 mL of methylene chloride. The organic phase was washed with 40 mL of water, dried with sodium sulfate, and concentrated to 5.90 g of yellow solid. The solid was first purified by flash chromatography (500 g of silica, ethyl acetate) and the product obtained was then slurried in 100 mL of methyl tert-butyl ether to provide 3.70 g (60%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a yellow solid. nmr (500 MHz, CDCl3) δ1.12 (t, J=7.5 Hz, 3H), 2.52 (s, 3H), 2.91 (q, J=7.5 Hz, 2H), 3.78 (s, 3H), 5.02 (s, 2H), 5.46 (s, 2H), 5.66 (s, 1H), 6.56 (s, 1H), 7.16.(d, J=6.9 Hz, 2H), 7.28 (m, 3H)

Provenance & Evidence