2-Phenylethanol → 2-Phenethyloxy-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277125Notes

Reaction equation

HRID 277125 reaction equation
[Na].CS([C:5]1[N:20]=[C:8]2[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:11]=[C:12]([NH2:13])[N:7]2[N:6]=1)=O.[C:21]1([CH2:27][CH2:28][OH:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:28]([O:29][C:5]1[N:20]=[C:8]2[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:11]=[C:12]([NH2:13])[N:7]2[N:6]=1)[CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 60542-PhenylethanolHCID 5360545SodiumHCID 226297032-Methanesulfinyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 226296562-Phenethyloxy-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineYield 83%

Procedure

0.06 g (0.003 mol) sodium in 50 ml 2-phenylethanol were stirred overnight at 60° C. 0.2 g (0.0007 mol) 2-methanesulfinyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine added and stirring was continued at 160° C. for 16 hours. Evaporation of the solvent and chromatography on silicagel with ethylacetate gave 0.2 g (83%) 2-phenethyloxy-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine, MS m/e (%):332 (M+H+,100).

Workup

  1. customEvaporation of the solvent and chromatography on silicagel with ethylacetate

Sources & evidence

ORD record
ord-36d3807a0e754f628f4cc523a3fee4bd
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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