Potassium Hydroxide → But-3-enyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine

HRID 277038Notes

Reaction equation

HRID 277038 reaction equation
[C:1]1([C:7]2[N:22]=[C:10]3[CH:11]=[C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[CH:13]=[C:14]([NH2:15])[N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Br[CH2:26][CH2:27][CH:28]=[CH2:29].C(=O)(O)[O-].[Na+]>CS(C)=O>[CH2:29]([NH:15][C:14]1[N:9]2[N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:22]=[C:10]2[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:13]=1)[CH2:28][CH:27]=[CH2:26]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 21241Homoallyl bromideHCID 516892Sodium BicarbonateHCID 226297002-Phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 9884418But-3-enyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amineYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.20 g (0.0007 mol) 2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine in 17.5 ml dimethylsulfoxide was treated with 0.69 g (0.001 mol) potassiumhydroxide(85%) for 20 minutes at room temperature. Then 0.10 g(0.0007 mol) 4-bromo-1-butene were added and stirring was continued for 40 hours. Saturated aqueous sodiumbicarbonate was added and the mixture was extracted with ethylacetate. Evaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 97/3 gave 0.04 g(17%) but-3-enyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine as beige crystals. MS m/e (%): 341 (M+, 21), 300 (100), 287 (65).

Workup

  1. extractionthe mixture was extracted with ethylacetate
  2. customEvaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 97/3

Sources & evidence

ORD record
ord-12a5289fdaa4414c987a317f989ef651
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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