Aluminum;lithium → HCID 178519987, compound

HRID 2397713Notes

Reaction equation

HRID 2397713 reaction equation
[OH:1][C:2]1[C:3]([C:8](O)=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[Al].[Li]>O1CCCC1>[OH:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 16211445Aluminum;lithiumHCID 178524895HCID 178524895, compound

Product 1

HCID 178519987HCID 178519987, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxypyrazine-2-carboxylic acid is converted to the methyl ester and the ester is reduced with lithium aluminium hyride in tetrahydrofuran to give 3-hydroxy-2-hydroxymethylpyrazine. Treatment of 3-hydroxy-2-hydroxymethylpyrazine at room temperature with thionyl chloride gives 3-hydroxy-2-chloromethylpyrazine and reacting this intermediate with cysteamine by the procedure of Example 62 gives 2-[(2-aminoethyl)thiomethyl]-3-hydroxypyrazine.

Sources & evidence

ORD record
ord-b5e11697b2284d7c80d5fbffd59cd83b
Source dataset
uspto-grants-1977_05
Patent number
US04022797

Reaction notes

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