N,N-Dimethylaniline → 5-Acetoxymethyl7-chloro-2-methyl-s-triazolo[1,5-a]pyrimidine

HRID 1032587Notes

Reaction equation

HRID 1032587 reaction equation
CN(C)C1C=CC=CC=1.[C:10]([O:13][CH2:14][C:15]1[CH:20]=[C:19](O)[N:18]2[N:22]=[C:23]([CH3:25])[N:24]=[C:17]2[N:16]=1)(=[O:12])[CH3:11].C(Cl)(Cl)[Cl:27]>P(Cl)(Cl)(Cl)=O>[C:10]([O:13][CH2:14][C:15]1[CH:20]=[C:19]([Cl:27])[N:18]2[N:22]=[C:23]([CH3:25])[N:24]=[C:17]2[N:16]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6212ChloroformHCID 178475878HCID 178475878, compound

Product 1

HCID 156727765-Acetoxymethyl7-chloro-2-methyl-s-triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
50 °C

Procedure

In 300 ml of phosphorus oxychloride was added dropwise 40 ml of N,N-dimethylaniline, and 35 g of 5-acetoxymethyl-7-hydroxy-2-methyl-s-triazolo[1,5-a]pyrimidine was added to the mixture and the mixture was stirred at 50° C. for one hour. An oily residue obtained by removing phosphorus oxychloride was dissolved in 500 ml of chloroform and ice-cooled. After addition of crushed ice and water to the mixture and stirring thereof, a chloroform layer was separated, washed with water and dried over anhydrous magnesium sulfate. Then, removing a solvent, an oily product was obtained. This was applied to a silica gel column chromatography (eluent: chloroform) and fractions containing the title compound were condensed to obtain an oily product. This was allowed to stand to cool and crystallized to obtain 31 g of the title compound.

Workup

  1. additionwas added to the mixture
  2. customAn oily residue obtained
  3. customby removing phosphorus oxychloride
  4. dissolutionwas dissolved in 500 ml of chloroform
  5. temperatureice-cooled
  6. additionAfter addition of crushed ice and water to the mixture
  7. stirringstirring
  8. customa chloroform layer was separated
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThen, removing a solvent
  12. customan oily product was obtained

Sources & evidence

ORD record
ord-9939fc528c964ac0a91fdba4030d4e06
Source dataset
uspto-grants-1990_09
Patent number
US04958019

Reaction notes

Loading…