Acetic Anhydride → N-[6-Chloro-2-(methylsulfanyl)pyrimidin-4-yl]acetamide

HRID 2233839Notes

Reaction equation

HRID 2233839 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]=[C:11]([NH2:17])[CH:10]=1>C(=O)(O)[O-].[Na+]>[Cl:8][C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]=[C:11]([NH:17][C:5](=[O:7])[CH3:6])[CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 704964-Amino-6-chloro-2-methylthiopyrimidine

Product 1

HCID 13447564N-[6-Chloro-2-(methylsulfanyl)pyrimidin-4-yl]acetamideYield 120.4%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
135 °C

Procedure

Acetic anhydride (10.4 ml, 0.11 mol) was added to 6-chloro-2-(methylthio)pyrimidin-4-amine (2.5 g, 0.01 mol) and the reaction mixture was refluxed at 135° C. for 5 hr. The reaction mixture was cooled to room temperature and basified to pH 7 with saturated sodium bicarbonate solution (20 ml). The mixture was partitioned between EtOAc and water, the organic layer was washed with water and brine, dried over MgSO4 and concentrated to give the title compound (2.62 g).

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-172ca628a4f245ff8186184e9427b582
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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