Sodium Azide → 1-(4-azidophenyl)pyrimidin-2(1H)-one

HRID 642980Notes

Reaction equation

HRID 642980 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]2=[O:14])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[N-:19]=[N+:20]=[N-].[Na+]>C(O)(C(F)(F)F)=O.O>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]2=[O:14])=[CH:6][CH:7]=1)=[N+:19]=[N-:20]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 592600731-(4-aminophenyl)pyrimidin-2(1H)-one

Product 1

HCID 592600781-(4-azidophenyl)pyrimidin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1-(4-Aminophenyl)pyrimidin-2(1H)-one (2.3, 250 mg, 1.3 mmol) was dissolved in 10 mL TFA and stirred in ice bath. To it was added sodium nitrite (95 mg, 1.3 mmol) in small portions. The mixture was stirred in ice bath for 30 min. Sodium azide (260 mg, 4.0 mmol) was dissolved in 2 mL water and chilled in ice bath and added to the reaction mixture. The mixture was stirred for 2 hrs and directly subjected to reverse phase prep HPLC to isolate 1-(4-azidophenyl)pyrimidin-2(1H)-one 2.4. MS found for C10H7N5O (M+H)+ 214.1.

Workup

  1. stirringThe mixture was stirred in ice bath for 30 min
  2. temperaturechilled in ice bath
  3. additionadded to the reaction mixture
  4. stirringThe mixture was stirred for 2 hrs

Sources & evidence

ORD record
ord-6503b7f9b5364784a390b8db95c2caa7
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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