Sodium Azide → (5-Azidomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine

HRID 2216278Notes

Reaction equation

HRID 2216278 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]([CH2:14]Cl)=[CH:4][N:3]=1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:16]([CH2:14][C:5]1[C:6]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)=[N+:17]=[N-:18]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 219418692-Chloro-5-(chloromethyl)-N-(2,2-dimethylpropyl)pyrimidin-4-amine

Product 1

HCID 21941878(5-Azidomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 1.47 g (5.92 mmol) of (2-chloro-5-chloromethyl-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine and 0.46 g (7.1 mmol) NaN3 is dissolved in 6 ml of DMF and was stirred at 30° C. for 2.5 hours. Then the reaction mixture is cooled to rt., diluted with ethyl acetate and twice extracted with H2O. The organic layer is separated and dried over Na2SO4. Evaporation of the ethyl acetate yielded (5-azidomethyl-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine as white crystalls.

Workup

  1. temperatureThen the reaction mixture is cooled to rt
  2. extractiontwice extracted with H2O
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-f65650acb2624ece9cd0d2b71f68c811
Source dataset
uspto-grants-2006_09
Patent number
US07112589B2

Reaction notes

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