Sodium borohydride → (2-Chloro-5-methylpyridin-3-yl)methanol

HRID 413477Notes

Reaction equation

HRID 413477 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1.[BH4-].[Na+]>>[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde

Product 1

HCID 12056721(2-Chloro-5-methylpyridin-3-yl)methanol

Procedure

comprising reducing 2-chloro-5-methylpyridine-3-carbaldehyde with sodium borohydride to give 2-chloro-3-hydroxymethyl-5-methylpyridine, followed by reacting the 2-chloro-3-hydroxymethyl-5-methylpyridine thus obtained with thionyl chloride to give 2-chloro-3-chloromethyl-5-methylpyridine, followed by reacting the 2-chloro-3-chloromethyl-5-methylpyridine thus obtained with 2-nitroimino-1,3-diazacyclopentane in the presence of a base and an organic solvent, to give 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine.

Sources & evidence

ORD record
ord-b897a3831f2d4654aa74c2acd25446d6
Source dataset
uspto-grants-2003_05
Patent number
US06566528B1

Reaction notes

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