Phosphorus oxychloride → 2-Acetoxymethyl7-chloro-5-methoxycarbonyl-s-triazolo[1,5-a]pyrimidine

HRID 1755912Notes

Reaction equation

HRID 1755912 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:19]=[C:9]2[NH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:13](=O)[N:8]2[N:7]=1)(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:22])=O>>[C:1]([O:4][CH2:5][C:6]1[N:19]=[C:9]2[N:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[C:13]([Cl:22])[N:8]2[N:7]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178498585HCID 178498585, compound

Product 1

HCID 156727662-Acetoxymethyl7-chloro-5-methoxycarbonyl-s-triazolo[1,5-a]pyrimidine

Procedure

Methyl 2-(acetoxymethyl)-4,7-dihydro-7-oxo-s-triazolo[1,5-a]pyrimidine-5-carboxylate (500 mg) (1.87 mmol) are suspended in 20 l of phosphorus oxychloride. The suspension is held under reflux for 5 hours. The mixture is concentrated in a water-jet vacuum, the residue is treated with dichloromethane and ice/water and extracted several times with dichloromethane. After drying and evaporation of the extract the product is crystallized from methanol. There are obtained 400 mg of methyl 2-(acetoxymethyl)-7-chloro-s-triazolo[1,5-a]pyrimidine-5-carboxylate.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThe mixture is concentrated in a water-jet vacuum
  3. additionthe residue is treated with dichloromethane and ice/water
  4. extractionextracted several times with dichloromethane
  5. customAfter drying
  6. customevaporation of the
  7. extractionextract the product
  8. customis crystallized from methanol

Sources & evidence

ORD record
ord-74054c66c0a949139b4d8a3f09cb28a1
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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