Potassium Carbonate → HCID 136110818, compound

HRID 1382900Notes

Reaction equation

HRID 1382900 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[C:32]1([CH3:38])[CH2:36][O:35][C:34](=[O:37])[O:33]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]([C:32]3([CH3:38])[CH2:36][O:35][C:34](=[O:37])[O:33]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

HCID 11430Potassium CarbonateHCID 21273651HCID 21273651, compoundHCID 178440702HCID 178440702, compound

Product 1

HCID 136110818HCID 136110818, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution 3.2 g of the compound of Example 1 in 20 ml of dimethylformamide are added 2 g of potassium carbonate and 1.6 g of 4-chloro-4-methyl-2-oxo-1,3-dioxolane, and the mixture is stirred at 60° C. for 6 hours. The reaction mixture is poured into ice-cold water and the precipitate is extracted with ethyl acetate. After the extract is washed with water, dried and concentrated, the residue is recrystallized from a mixed solvent of hexane and toluene to give 3 g of 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-1H-pyrazolo[3,4-b]pyridine as white crystals, melting at 190°-191° C.

Workup

  1. additionThe reaction mixture is poured into ice-cold water
  2. extractionthe precipitate is extracted with ethyl acetate
  3. washAfter the extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue is recrystallized from a mixed solvent of hexane and toluene

Sources & evidence

ORD record
ord-055b0a50f4094552942ae3a3ae45e477
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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