Dimethyl 2,2-dimethyl-3-oxobutanedioate → HCID 178500128, compound

HRID 570542Notes

Reaction equation

HRID 570542 reaction equation
[CH3:1][C:2]([CH3:13])([C:7](=O)[C:8](OC)=[O:9])[C:3]([O:5][CH3:6])=[O:4].[F:14][C:15]1[CH:34]=[CH:33][CH:32]=[CH:31][C:16]=1[CH2:17][N:18]1[C:22]2=[N:23][CH:24]=[N:25][CH:26]=[C:21]2[C:20]([C:27](=[NH:30])[NH:28][NH2:29])=[N:19]1>C(O)C>[F:14][C:15]1[CH:34]=[CH:33][CH:32]=[CH:31][C:16]=1[CH2:17][N:18]1[C:22]2=[N:23][CH:24]=[N:25][CH:26]=[C:21]2[C:20]([C:27]2[N:28]=[N:29][C:7]([C:2]([CH3:13])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[C:8]([OH:9])[N:30]=2)=[N:19]1

Participants

4

Reactant 2

HCID 85519062Dimethyl 2,2-dimethyl-3-oxobutanedioateHCID 178512736HCID 178512736, compound

Product 1

HCID 178500128HCID 178500128, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

584 mg (3.103 mmol) of dimethyl 2,2-dimethyl-3-oxobutanedioate were initially charged in 12 ml of ethanol and heated to reflux. Subsequently, 590 mg (2.069 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidohydrazide suspended in 12 ml of ethanol were added and the mixture was boiled under reflux overnight. After cooling, the mixture was filtered, the filtercake was washed with a little ethanol and the filtrate was concentrated. The residue was stirred with 10 ml of acetonitrile. 188 mg of the target compound were obtained (purity 93%; 20% of theory).

Workup

  1. temperatureheated to reflux
  2. additionwere added
  3. temperatureunder reflux overnight
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered
  6. washthe filtercake was washed with a little ethanol
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c96436a4526b46e9be314f927866c1fe
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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