Dimethyl Sulfoxide → N-[(6-methylpyridin-2-yl)methyl]-N-pyridin-2-ylpyridin-2-amine

HRID 1970733

Reaction equation

HRID 1970733 reaction equation
[OH-].[K+].CS(C)=O.[CH:7]1[CH:12]=[C:11]([NH:13][C:14]2[N:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=[CH:9][CH:8]=1.[CH3:20][C:21]1[N:26]=[C:25]([CH2:27]Br)[CH:24]=[CH:23][CH:22]=1>O>[CH3:27][C:25]1[N:26]=[C:21]([CH2:20][N:13]([C:11]2[CH:12]=[CH:7][CH:8]=[CH:9][N:10]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:19]=2)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 145472,2'-DipyridylamineHCID 14797Potassium HydroxideHCID 125437332-(Bromomethyl)-6-methylpyridine

Product 1

HCID 66628202N-[(6-methylpyridin-2-yl)methyl]-N-pyridin-2-ylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask were added 0.6 g pulverized potassium hydroxide and 15 ml dimethylsulfoxide. After adding 1.4 g of 2,2′-dipyridylamine, the mixture was stirred under nitrogen for 45 minutes, when 1.5 g 6-methyl-2-(bromomethyl)pyridine was added. After stirring for 1 hour, 35 ml of water was added and the product was extracted with 60 ml of 50% ethyl acetate, 50% hexane. The organic layer was washed with 30 ml water and the solvent was removed. The residue was purified by silica gel chromatography using 48% ethyl acetate, 48% hexane, and 4% methanol resulting in 2.0 g of an oil.

Workup

  1. additionTo a flask were added 0.6 g
  2. stirringAfter stirring for 1 hour
  3. extractionthe product was extracted with 60 ml of 50% ethyl acetate, 50% hexane
  4. washThe organic layer was washed with 30 ml water
  5. customthe solvent was removed
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-faa27bf9f09e4feeb7427d393ce37fcc
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Linked notes

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