Diboron → (3-Chloro-5-methylpyrazin-2-yl)methanol

HRID 26845

Reaction equation

[Cl:1][C:2]1[C:3]([C:9](O)=[O:10])=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=1.B#B>>[Cl:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=1

Participants

Reactant 2

HCID 6328200Diboron

HCID 205579983-Chloro-5-methylpyrazine-2-carboxylic acid

Product 1

HCID 20557611(3-Chloro-5-methylpyrazin-2-yl)methanol

Procedure

Reduction of 3-chloro-5-methyl-2-pyrazinecarboxylic acid (prepared by alkaline hydrolysis of the methyl ester) with diborane gives 3-chloro-2-hydroxymethyl-5-methylpyrazine which, using the above procedure, yields N-methyl-N'-[2-((3-chloro-5-methyl-2-pyrazinyl)methylthio)ethyl]thiourea.

Sources & evidence

ORD record: ord-324645d3203042189d7320a49ef1caf8
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151288

Linked notes

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