Tetrahydrofuran → HCID 70622710, compound

HRID 1834592Notes

Reaction equation

HRID 1834592 reaction equation
O[C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:17]1CCCC1>>[OH:17][C:3]1([CH2:8][OH:10])[N:4]=[CH:5][CH:6]=[N:7][CH2:2]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 178524895HCID 178524895, compound

Product 1

HCID 70622710HCID 70622710, compound

Procedure

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

Sources & evidence

ORD record
ord-0a3260a66578477c8dd6eab02d7a16d0
Source dataset
uspto-grants-1978_01
Patent number
US04070475

Reaction notes

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