N,N-Dimethylaniline → 5-Acetoxymethyl7-chloro-2-methyl-s-triazolo[1,5-a]pyrimidine
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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-acetoxymethyl7-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
- additionwas added to the mixture
- customAn oily residue obtained
- customby removing phosphorus oxychloride
- dissolutionwas dissolved in 500 ml of chloroform
- temperatureice-cooled
- additionAfter addition of crushed ice and water to the mixture
- stirringstirring
- customa chloroform layer was separated
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- customThen, removing a solvent
- customan oily product was obtained
Sources & evidence
- ORD record
- ord-99dde5d1bba64bb89fdfcbb079f1f991
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04987129
Reaction notes
Loading…