Sodium hydride → HCID 22129650, compound

Participants

Reaction Steps

SODIUM HYDRIDE (40 MG OF A 60% DISPERSION IN MINERAL OILS, 1.0 MMOL) WAS ADDED TO A STIRRED SOLUTION OF 2-BROMO-3-HYDROXY-5-METHYLTHIOPYRAZINE (100 MG, 0.45 MMOL) IN DRY THF (10 ML) UNDER ARGON. T-BUTYL BROMOACTATE (202 MICROL, 1.5 MMOL) WAS ADDED AND THE REACTION WAS STIRRED FOR 16 H. THE VOLATILES WERE EVAPORATED IN VACUO AND THE RESIDUE WAS PARTITIONED BETWEEN WATER AND METHYLENE CHLORIDE. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO. THE CRUDE PRODUCT WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (30% ETHYL ACETATE/HEXANES) TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID:

Provenance & Evidence