Sulfuric Acid → 1-(Pyrimidin-4-yl)ethanone

HRID 1580445Notes

Reaction equation

HRID 1580445 reaction equation
[CH3:1][Mg]Cl.[N:4]1[CH:9]=[CH:8][C:7](C#N)=[N:6][CH:5]=1.S(=O)(=O)(O)O.[C:17](=[O:20])([O-])[O-].[Na+].[Na+]>CCOCC.O1CCCC1>[N:4]1[CH:9]=[CH:8][C:7]([C:17]([CH3:1])=[O:20])=[N:6][CH:5]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 10313094Pyrimidine-4-carbonitrileHCID 178418332HCID 178418332, compound

Product 1

HCID 5380601-(Pyrimidin-4-yl)ethanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 22.2 g. of methyl magnesium chloride in ether is added 10.5 g. of 4-pyrimidinecarbonitrile in tetrahydrofuran. The resulting mixture is heated at reflux for 24 hours, then poured onto ice. To the mixture is added 75 ml. of 25% sulfuric acid. The solution is then made basic with 10% aqueous sodium carbonate solution and extracted with ether. The extracts are dried and concentrated to give methyl 4-pyrimidyl ketone.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 24 hours
  3. additionpoured onto ice
  4. additionTo the mixture is added 75 ml
  5. extractionextracted with ether
  6. customThe extracts are dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a54c47214af1478d8919dc0eb05ccd04
Source dataset
uspto-grants-1976_01
Patent number
US03932641

Reaction notes

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