Aminopyrazine → 5-(Methylthio)pyrazin-2-amine

Participants

Reaction Steps

2-Amino-5-bromopyrazine can be prepared from aminopyrazine as described (Tetrahedron, Vol. 44, pp. 2977-2984 (1988)). Reaction of 2-amino-5-bromopyrazine with sodium methanethiolate proceeds to form 2-amino-5-methylthiopyrazine (J. Het. Chem., Vol. 28, pp. 1131-1137 (1991)). Oxidation of 2-amino-5-methylthiopyrazine with m-chloroperbenzoic acid produces 2-amino-5-methanesulfonylpyrazine. 2-Hydrazino-5-methanesulfonylpyrazine can be prepared by known procedures (J. Het. Chem., Vol. 27, pp. 2151-2163 (1990)). Subsequent reaction of 2-Hydrazino-5-methanesulfonylpyrazine with 4,4,4-trifluoro-1-(4-methoxyphenyl)-1,3-butanedione (made from 4-methoxyacetophenone and ethyl trifluoroacetate via Scheme 1) can then produce the title compound.

Provenance & Evidence