Ethanol → 1-(2-Aminopyridin-4-yl)ethanol
Reaction equation
N([C:3]1[N:8]=[C:7]([CH:9]([OH:11])[CH3:10])[CH:6]=[CH:5][N:4]=1)N.[CH2:12](O)C>CO.[Ni]>[NH2:8][C:3]1[CH:12]=[C:7]([CH:9]([OH:11])[CH3:10])[CH:6]=[CH:5][N:4]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
1-(2-hydrazinopyrimidin-4-yl)ethanol (13a) was dissolved in ethanol (300 mL) and Raney-Ni (35 mL, 50% slurry in water) was added. The flask was flushed with argon, put under a hydrogen atmosphere (balloon) and stirred at room temperature overnight. The mixture was filtered and concentrated under vacuum to give a red oil that was dissolved in methanol and concentrated onto silica before being purified by silica flash chromatography (100% ethyl acetate to 20% methanol in ethyl acetate) to give the title compound (9.0 g) as an orange oil.
Workup
- customThe flask was flushed with argon
- filtrationThe mixture was filtered
- concentrationconcentrated under vacuum
- customto give a red oil that
- concentrationconcentrated onto silica
- custombefore being purified by silica flash chromatography (100% ethyl acetate to 20% methanol in ethyl acetate)
Sources & evidence
- ORD record
- ord-e95419049608414fa222b2aac96e5390
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952001B2
Reaction notes
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