Sodium Azide → 5-(azidomethyl)-2,4(1H,3H)-pyrimidinedione

HRID 2211818Notes

Reaction equation

HRID 2211818 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1>CS(C)=O>[N:1]([CH2:6][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2361255-(Chloromethyl)uracil

Product 1

HCID 219630275-(azidomethyl)-2,4(1H,3H)-pyrimidinedioneYield 98.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium azide (0.6 g, 9.34 mmol) was added to a solution of 5-(chloromethyl)-2,4(1H,3H)-pyrimidinedione (0.3 g, 1.67 mmol) in DMSO (5 ml) under nitrogen at room temperature. The reaction was stirred for 2 h then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to give the 5-(azidomethyl)-2,4(1H,3H)-pyrimidinedione (0.275 g, 98%) as a yellow solid.

Workup

  1. customthen partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-22f7f1367d0f4603af5b503bf3ddbb77
Source dataset
uspto-grants-2006_09
Patent number
US07101883B2

Reaction notes

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