4-Toluenesulfonyl chloride → 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

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Reaction Steps

2,4-dichloro-5-iodo-1H-pyrrolo[2,3-d]pyrimidine (660 mg, 2.103 mmol) and tosyl-chloride (441 mg, 2.31 mmol) were combined in dry dichloromethane (20 ml). Diisopropylethylamine (0.734 mL, 4.21 mmol) was added and the reaction mixture was let stir at rt for 18 h. The reaction was then diluted with dichloromethane and the organic layer was washed with a saturated solution of sodium bicarbonate, water and a saturated solution of brine, then dried over sodium sulfate. Solvents were removed under reduced pressure and the residue purified by chromatography on SiO2 to afford 2,4-dichloro-5-iodo-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (901 mg, 1.94 mmol) as a yellow solid. ESIMS (M+H)+=469.

Provenance & Evidence