Ammonia → 4-Amino-2-chloro-7-pentofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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Reaction Steps

5-Cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (5, 2.85 g) was covered with 50 ml of liquid ammonia and the solution was allowed to stand at room temperature for 12 hr while sealed in a steel vessel. The excess ammonia was allowed to evaporate and the residue was triturated with 50 ml of cold water. The water insoluble solid was collected by filtration, washed with 10 ml of water and dissolved in a minimum amount of boiling methanol. The methanol solution was then concentrated to ~100 ml or until the product began to crystallize. The solution was then allowed to stand at -5° for 12 hr. The white to light tan crystalline solid was collected by filtration, washed with 15 ml of methanol and dried in a vacuum oven for 2 hr at 100° over drierite to yield 1.00 g (51%) of 6, mp 258-260° dec.

Provenance & Evidence