Potassium Carbonate → HCID 136203573, compound
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+].Cl[CH2:32][CH:33]1[CH2:37][O:36][C:35](=[O:38])[O:34]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]([CH2:32][CH:33]3[CH2:37][O:36][C:35](=[O:38])[O:34]3)[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
- 65 °C
Procedure
To a solution of 6.5 g of the compound of Example 1 in 50 ml of dimethylformamide are added 4.1 g of potassium carbonate and 4.1 g of 4-chloromethyl-2-oxo-1,3-dioxolane, and the mixture is stirred at 65° C. for 4 hours. After completion of the reaction, the reaction mixture is poured into ice-cold water, and the precipitate is extracted with ethyl acetate. The extract is washed with water, dried and concentrated, and then the obtained residue is recrystallized from isopropyl ether to give 6 g of 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(2-oxo-1,3-dioxolan-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridine as white crystals, melting at 140°-141° C.
Workup
- customAfter completion of the reaction
- additionthe reaction mixture is poured into ice-cold water
- extractionthe precipitate is extracted with ethyl acetate
- washThe extract is washed with water
- customdried
- concentrationconcentrated
- customthe obtained residue is recrystallized from isopropyl ether
Sources & evidence
- ORD record
- ord-22dfb097ae2a4db39997b12c96564205
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808620
Reaction notes
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