Hydrochloric Acid → HCID 178419009, compound

HRID 1505474Notes

Reaction equation

HRID 1505474 reaction equation
CC1C=C(O)N2N=CC=C2N=1.CC1C=C(O)N2C=CN=C2N=1.[CH3:23][C:24]1[CH:29]=[C:28]([OH:30])[N:27]2[N:31]=[CH:32][N:33]=[C:26]2[N:25]=1.P(Cl)(Cl)(Cl)=O.Cl>>[CH3:23][C:24]1[CH:29]=[C:28]([OH:30])[N:27]2[N:31]=[CH:32][N:33]=[C:26]2[N:25]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 178429154HCID 178429154, compound

Product 1

HCID 178419009HCID 178419009, compoundYield 42%

Procedure

5-Methyl-pyrazolo[1,5-a]pyrimidin-7-ol/7-Methyl-imidazo[1,2-a]pyrimidin-5-ol/5-Methyl-[1,2,4]triazolo[1,5-a]-pyrimidin-7-ol (C) (6.5 mmol) was added to 1.82 ml (19.5 mmol) of phosphorus oxychloride and heated under reflux for 30-60 minutes. in a round bottom flask, during which time the solid dissolved and hydrogen chloride was evolved. Excess phosphorus oxychloride was removed by distillation at reduced pressure on a steam-bath and the residue triturated with ice water. Product was extracted from the aqueous mixture with methylene chloride, evaporated and purified by column chromatography using 60% EtOAc/Hexane at a yield of 42-70%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30-60 minutes
  3. dissolutionin a round bottom flask, during which time the solid dissolved
  4. customExcess phosphorus oxychloride was removed by distillation at reduced pressure on a steam-bath
  5. customthe residue triturated with ice water
  6. extractionProduct was extracted from the aqueous mixture with methylene chloride
  7. customevaporated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-ff1f5931aca945c98de90fb1aa2c9b50
Source dataset
uspto-grants-2015_12
Patent number
US09216983B2

Reaction notes

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