Acetic Anhydride → HCID 59797350, compound

HRID 243335Notes

Reaction equation

HRID 243335 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:12])[CH3:11])=[CH:4][N:3]=1.C([O-])(=O)C.[K+].C(OC(=O)C)(=O)C.[N:25](OCCC(C)C)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:9]([C:10](=[O:12])[CH3:11])[N:25]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 23070222N-(2-Chloro-4-methylpyrimidin-5-yl)acetamide

Product 1

HCID 59797350HCID 59797350, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-(2-chloro-4-methylpyrimidin-5-yl)acetamide (9 g, 46.06 mmol, 1.00 equiv, 95%), potassium acetate (3.3 g, 32.95 mmol, 0.72 equiv, 98%), acetic anhydride (17.27 g, 165.78 mmol, 3.60 equiv) and isoamyl nitrite (13.6 g, 116.24 mmol, 2.52 equiv, 98%) in chloroform (180 mL) was reflux overnight. The resulting mixture was washed with water, dried over anhydrous sodium sulfate and concentrated under vacuum to give 7 g (73%) of 1-[5-chloro-1H-pyrazolo[4,3-d]pyrimidin-1-yl]ethan-1-one as a white solid.

Workup

  1. washThe resulting mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cc19c3e1b37c4886a466613f23eea767
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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