Dimethylformamide → 2-{6-Azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

HRID 2302

Reaction equation

HRID 2302 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[N-:19]=[N+:20]=[N-:21].[Na+].CN(C)C=O>O>[N:19]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 111189672-{6-Chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

Product 1

HCID 118077902-{6-Azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanolYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (21.85 g), sodium azide (10.7 g) and dimethyformamide (260 ml) is heated with stirring at 75°-80° C. overnight. After cooling, the mixture is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from hexane to give 2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol (19.6 g).

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is crystallized from hexane

Sources & evidence

ORD record
ord-c78f869bf2a74b75ba8846f932a65794
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

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