6-Methyl-2-pyridylmethanol → 7-(6-Methyl-pyridin-2-ylmethoxy)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277090Notes

Reaction equation

HRID 277090 reaction equation
Br[C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:11]=[C:4]2[CH:3]=1.[CH3:18][C:19]1[N:24]=[C:23]([CH2:25][OH:26])[CH:22]=[CH:21][CH:20]=1>CN1CCCC1=O>[CH3:18][C:19]1[N:24]=[C:23]([CH2:25][O:26][C:2]2[CH:7]=[C:6]([NH2:8])[N:5]3[N:9]=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=4)[N:11]=[C:4]3[CH:3]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 707366-Methyl-2-pyridylmethanolHCID 226297067-Bromo-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 226297207-(6-Methyl-pyridin-2-ylmethoxy)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1 eq. 7-bromo-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine, 5 eq. (6-methyl-pyridin-2-yl)-methanol and a catalytic amount of CS2CO3 in 200 μl N-methyl-pyrrolidon was heated for 2 h to 160°. The mixture was, after filtration, purified with reversed phase column chromatography eluting with an acetonitrile/water gradient yielding the title compound, MS m/e (%): 332 M+H+ (100%).

Workup

  1. additionA mixture of 1 eq
  2. filtrationafter filtration
  3. custompurified with reversed phase column chromatography
  4. washeluting with an acetonitrile/water

Sources & evidence

ORD record
ord-52fdf304478d49b0a97cec170be12683
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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