1-Bromo-3-methylbutane → HCID 86734968, compound

HRID 259406Notes

Reaction equation

HRID 259406 reaction equation
[OH:1][C:2]1[C:3]2[C:4](=[N:13][N:14]([CH3:16])[CH:15]=2)[N:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].Br[CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:16][N:14]1[CH:15]=[C:3]2[C:4]([N:5]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]2=[O:1])=[N:13]1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 178469710HCID 178469710, compound

Product 1

HCID 86734968HCID 86734968, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.1 g. of 4-hydroxy-2-methyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester (0.1 mol.), 17 g. of 1-bromo-3-methylbutane and 21 g. of potassium carbonate are heated together with stirring in 100 ml. of dimethylformamide at 100° for 12 hours. The mixture is filtered hot, evaporated to dryness and the residue recrystallized from ethyl acetate to obtain 4,7-dihydro-2-methyl-7-(3-methylbutyl)-4-oxo-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester, yield (63%); m.p. 105°-106°.

Workup

  1. filtrationThe mixture is filtered hot
  2. customevaporated to dryness
  3. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fe8d0aa8b59f4863bcc75c91dcbfccae
Source dataset
uspto-grants-1977_07
Patent number
US04038281

Reaction notes

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