1-Ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea → 1-Ethyl-3-(5-formyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea
Reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:23]=[C:10]2[CH:11]=[C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:13]=[C:14]([CH2:15][OH:16])[N:9]2[N:8]=1)=[O:5])[CH3:2]>C1COCC1.O=[Mn]=O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:23]=[C:10]2[CH:11]=[C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:13]=[C:14]([CH:15]=[O:16])[N:9]2[N:8]=1)=[O:5])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The product of Step 1 (154 mg, 0.50 mmol) was dissolved in THF (50 mL), to which was added MnO2 (250 mg). This mixture was heated at reflux for 18 h., at which point two further portions (50 mg each) were added over the next 8 hours. Finally, the mixture was heated at reflux for 18 h., allowed to cool, then the MnO2 removed by filtration over celite which was washed with THF and MeOH/CH2Cl2. The solvent was removed under reduced pressure to afford 1-ethyl-3-(5-formyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea as a crude solid. LCMS (APCI+) 311.
Workup
- temperatureThis mixture was heated
- temperatureat reflux for 18 h., at which point two further portions (50 mg each)
- additionwere added over the next 8 hours
- temperatureFinally, the mixture was heated
- temperatureat reflux for 18 h.
- temperatureto cool
- customthe MnO2 removed by filtration over celite which
- washwas washed with THF and MeOH/CH2Cl2
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-8b21061d454c4793b89cf04555bcf3b2
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524860B2
Reaction notes
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