Acetic Acid → 5-Amino-4,6-bis(dimethylamino)pyrimidine

HRID 1756782Notes

Reaction equation

HRID 1756782 reaction equation
C(O)(=O)C.CC(O)C.[CH3:9][N:10]([CH3:23])[C:11]1[C:16]([N+:17]([O-])=O)=[C:15]([N:20]([CH3:22])[CH3:21])[N:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>O.[Fe].CC(C)=O>[NH2:17][C:16]1[C:11]([N:10]([CH3:23])[CH3:9])=[N:12][CH:13]=[N:14][C:15]=1[N:20]([CH3:21])[CH3:22]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 2822931N4,N4,N6,N6-tetramethyl-5-nitro-4,6-pyrimidinediamine

Product 1

HCID 155853705-Amino-4,6-bis(dimethylamino)pyrimidineYield 91.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 5 g of iron dust, 0.5 g of acetic acid and 3.5 ml of water was refluxed under heating for 30 minutes, allowed to cool at 80° C. and mixed with 14 ml of 2-propanol and gradually mixed with 4.22 g of 4, 6-bis (dimethylamino)-5-nitropyrimidine. The resultant mixture was stirred at the same temperature for 1 hour, allowed to cool at 40° C., mixed with a solution of 1.5 g of potassium carbonate in 2.5 ml of water and stirred for 1 hour. Acetone was added to the mixture, which was filtered through Celite. The filtrate was concentrated in vacuo, and the residue was mixed with water and shaken with ether. The organic layer was washed with water and saturated saline in order, dried over anhydrous sodium sulfate and the solvent evaporated to give 3.32 g of the titled compound.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 30 minutes
  3. temperatureto cool at 40° C.
  4. filtrationwas filtered through Celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionthe residue was mixed with water
  7. stirringshaken with ether
  8. washThe organic layer was washed with water and saturated saline in order
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-f2009cb5386841eca04becab424c160c
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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