Acetic Anhydride → N-(2,6-dichloropyrimidin-4-yl)acetamide

HRID 2233809

Reaction equation

HRID 2233809 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.C([O-])(O)=O.[Na+].[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[Cl:9][C:4]1[N:3]=[C:2]([NH:1][C:15](=[O:17])[CH3:16])[CH:7]=[C:6]([Cl:8])[N:5]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 823874-Pyrimidinamine, 2,6-dichloro-HCID 516892Sodium Bicarbonate

Product 1

HCID 4713752N-(2,6-dichloropyrimidin-4-yl)acetamideYield 80%

Procedure

4-Amino-2,6-dichloropyrimidine (500 mg, 3.05 mmol) was refluxed in acetic anhydride (10 ml) for 3 h. Upon cooling to room temperature, the reaction mixture was cooled in an ice bath and basified to pH 8 with 10% aqueous NaHCO3. The phases were separated, and the aqueous portion was extracted twice with EtOAc. The combined organic portions were dried over Na2SO4, filtered, and concentrated to give an off-white solid (503.7 mg, 2.44 mmol, 80% yield).

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. customThe phases were separated
  3. extractionthe aqueous portion was extracted twice with EtOAc
  4. dry with materialThe combined organic portions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c1a94b172384472c8dda843e419df92c
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Linked notes

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