Ammonium Chloride → 2-Amino-5,6-dichloro-3-[hydroxy(thiazol-2-yl)methyl]pyrazine

Participants

Reaction Conditions

Reaction Steps

In 5 ml of ether there was dissolved 2-amino-5,6-dichloro-3-formylpyrazine (144 mg; 0.75 mMol) prepared as in Example 1, Step B above. The (thiazol-2-yl)lithium (1 mMol) prepared in Step A above was cooled to -78° C., after which the solution of 2-amino-5,6-dichloro-3-formylpyrazine was added dropwise under nitrogen. The reaction mixture was then allowed to warm up gradually to -15° C. and kept at that temperature for 30 minutes. When thin layer chromatography indicated substantial amounts of starting material remaining, additional (thiazol-2-yl)lithium was added. Ammonium chloride solution was then added and the reaction mixture was stirred for 15 minutes at -15° C. The mixture was extracted with ether, passed through a silica gel column, and eluted with dichloromethane to give the product (44 mg).

Provenance & Evidence