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

HRID 1860592Notes

Reaction equation

HRID 1860592 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.NC1C=NC=CN=1.[CH3:16][S-:17].[Na+]>>[NH2:1][C:2]1[CH:7]=[N:6][C:5]([S:17][CH3:16])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 78747AminopyrazineHCID 5995392-Amino-5-bromopyrazine2×HCID 4378561Sodium methanethiolate

Product 1

HCID 218972225-(Methylthio)pyrazin-2-amine

Procedure

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.

Sources & evidence

ORD record
ord-06584c2c97e04bd4b959ef74005ad2c8
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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