Dimethyl Disulfide → 4-Chloro-5-(methylsulfanyl)-7H-pyrrolo[2,3-D]pyrimidine

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Reaction Steps

To 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.18 g, 0.77 mmol) in dry THF (2 ml), cooled in a dry ice-acetone bath, was added dropwise n-butyllithium (0.77 ml, 1.9 mmol, 2.5 M in hexanes). The mixture was stirred for 1 hour, then dimethyldisulfide (0.077 mL, 0.77 mmol) suspended in dry THF (1 ml) was added. The solution was stirred for 2.5 hours at −78° C. and then diluted with aqueous NH4Cl. The phases were separated and the water extracted 2 times with ethyl acetate. The combined organic phases were dried over Na2SO4, and concentrated in vacuo to afford 4-chloro-5-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine as an orange solid (150 mg).

Provenance & Evidence