Sodium borohydride → (5-Chloro-6-methylpyridin-2-YL)methanamine

HRID 530802Notes

Reaction equation

HRID 530802 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8].[BH4-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][NH2:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 573365975-Chloro-6-methylpyridine-2-carbonitrile

Product 1

HCID 72214042(5-Chloro-6-methylpyridin-2-YL)methanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of 5-chloro-6-methylpicolinonitrile (3) (200 mg, 1.31 mmol) in MeOH (10 mL) was added NaBH4 (150 mg, 3.94 mmol), CoCl2 (5 mg) at room temperature. After 30 min, the mixture was filtered and purified by reverse phase chromatography (X bridge Prep C18OBD, 40-60% MeOH in water with 10 mmol NH4HCO3 modifier) to afford the compound as an oil.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-04b217567ed54c7c9f8e2180148604cc
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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