Phosphorus oxychloride → 4-chloro-5H-pyrrolo[3,2-d]pyrimidine

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Reaction Steps

Into a 50-mL round-bottom flask was placed a solution of 3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (5 g, 35.52 mmol, 1.00 equiv, 96%) in trichlorophosphate (20 mL). The resulting solution was stirred at reflux for 1 h, concentrated under vacuum, dissolved in 100 mL of ethyl acetate, washed with 2×100 mL of 10% aqueous sodium bicarbonate and 1×100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluted with ethyl acetate/petroleum ether (1:8) to afford 2 g (36%) of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine as a yellow solid.

Provenance & Evidence