N,N-Dimethylaniline → 7-Chloro-2,5-bis(acetoxymethyl)-s-triazolo[1,5-a]pyrimidine
Reaction equation
CN(C)C1C=CC=CC=1.[C:10]([O:13][CH2:14][C:15]1[N:29]=[C:18]2[N:19]=[C:20]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH:21]=[C:22](O)[N:17]2[N:16]=1)(=[O:12])[CH3:11].C(Cl)(Cl)[Cl:31]>P(Cl)(Cl)(Cl)=O>[Cl:31][C:22]1[N:17]2[N:16]=[C:15]([CH2:14][O:13][C:10](=[O:12])[CH3:11])[N:29]=[C:18]2[N:19]=[C:20]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH:21]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
In 300 ml of phosphorus oxychloride was added dropwise 28 ml of N,N-dimethylaniline, and 30.5 g of 2,5-bis(acetoxymethyl)-7-hydroxy-s-triazolo[1,5-a]pyrimidine was added to the mixture and the mixture was stirred at 50° C. for 1.5 hours. 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, the mixture was condensed. This was applied to a silica gel column chromatography (eluent: chloroform) and fractions containing the title compound were condensed to obtain 14 g of the title compound as an oily product.
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
- customcondensed
Sources & evidence
- ORD record
- ord-608976e894a44bae944fe9411f0412b4
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04956462
Reaction notes
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