Potassium Carbonate → 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(2-methoxyethyl)-1H-pyrazolo[3,4-b]pyridine
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH2:41][CH2:42][O:43][CH3:44])(=O)=O)=CC=1>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:41][CH2:42][O:43][CH3:44])[N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 7.8 g of 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine in 40 ml of dimethylformamide are added 4.9 g of potassium carbonate and 7.2 g of 2-methoxyethyl p-toluenesulfonate, and the mixture is stirred at 60° C. for 7 hours. The resulting mixture is poured into ice-cold water and the precipitate is extracted with toluene. The extract is washed with water, dried and concentrated. The residue is recrystallized from hexane to give 7.2 g of 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(2-methoxyethyl)-1H-pyrazolo[3,4-b]pyridine as white crystals, melting at 111°-113° C.
Workup
- additionThe resulting mixture is poured into ice-cold water
- extractionthe precipitate is extracted with toluene
- washThe extract is washed with water
- customdried
- concentrationconcentrated
- customThe residue is recrystallized from hexane
Sources & evidence
- ORD record
- ord-4e2e0e2d457545d188649f0a81b4cef8
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808620
Reaction notes
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