2-(6-Amino-8-(2-pyridin-3-yl-ethynyl)-purin-9-yl)ethanol → 2-(6-Amino-8-(2-pyridin-3-yl-ethyl)-purin-9-yl)ethanol

HRID 1920655Notes

Reaction equation

HRID 1920655 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:14]#[C:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[N:6]2[CH2:11][CH2:12][OH:13]>CO.[Ni]>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[N:6]2[CH2:11][CH2:12][OH:13]

Participants

4

Reactant 1

HCID 668679042-(6-Amino-8-(2-pyridin-3-yl-ethynyl)-purin-9-yl)ethanol

Product 1

HCID 668676282-(6-Amino-8-(2-pyridin-3-yl-ethyl)-purin-9-yl)ethanolYield 41%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 1.1 g of 2-(6-amino-8-(2-pyridin-3-yl-ethynyl)-purin-9-yl)ethanol in 400 ml methanol were added 2.0 g of Raney-nickel and the mixture was hydrogenated (4 atm) at 80° C. during 6 hours. After completion of the reaction the catalyst was removed and the solvent was evaporated. The crude product was purified by column chromatography on silica gel (CHCl3:MeOH 9:1) to give 0.45 g (41%) of the desired product.

Workup

  1. customat 80° C.
  2. customduring 6 hours
  3. customAfter completion of the reaction the catalyst
  4. customwas removed
  5. customthe solvent was evaporated
  6. customThe crude product was purified by column chromatography on silica gel (CHCl3:MeOH 9:1)

Sources & evidence

ORD record
ord-b03f355c1136459687e27d8a18741cfe
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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