7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- → 4-Methoxy-7h-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium methoxide prepared by adding portion wise the sodium (2 g) in methanol (100 mL) under an inert atmosphere, was added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (Reference: Gerster, John F.; Hinshaw, Barbara C.; Robins, Roland K.; Townsend, Leroy B. Study of electrophylic substitution in the pyrrolo[2,3-d]pyrimidine ring. J. Heterocycl. Chem. (1969), -(2), 207-13.) (3.5 g). The solution was stirred at 65° C. for 16 hours and then partitioned between ethyl acetate and brine. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (50:50, v/v) to give the title compound (1.2 g) as an amorphous solid. MS: 150 [MH]+. LCMS (Method B) RT=2.39 minutes.

Provenance & Evidence