Phosphorus oxychloride → 5-Chloro-7-methylimidazo[1,2-a]pyrimidine

HRID 591253Notes

Reaction equation

HRID 591253 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[N:5]2[CH:9]=[CH:10][N:11]=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:14])=O>C(Cl)Cl>[Cl:14][C:6]1[N:5]2[CH:9]=[CH:10][N:11]=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429153HCID 178429153, compound

Product 1

HCID 151165185-Chloro-7-methylimidazo[1,2-a]pyrimidineYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.893 g (5.99 mmol) 7-Methylimidazo[1,2-a]pyrimidin-5-ol and 17 mL (182.1 mmol) of phosphorus oxychloride were refluxed for two hours. At the end of the reflux, a clear red solution is obtained, which is rotovaped to remove excess phosphorus oxychloride. The residue thus obtained was titurated with methylene chloride followed by filtration of the slurry to isolate the desired compound as a solid. Further washes with methylene chloride followed by drying of the solid under reduced pressure resulted in the chlorinated product. Yield 522 mg (52% yield).

Workup

  1. temperaturewere refluxed for two hours
  2. customAt the end of the reflux, a clear red solution is obtained
  3. customto remove excess phosphorus oxychloride
  4. customThe residue thus obtained
  5. filtrationfollowed by filtration of the slurry

Sources & evidence

ORD record
ord-ba22f1d95796412ea08667cb1b7c5c45
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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