N,N-Dimethylaniline → Methyl 7-chloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylate

HRID 1089526Notes

Reaction equation

HRID 1089526 reaction equation
O[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1.P(Cl)(Cl)([Cl:18])=O.CN(C)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:18][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178498583HCID 178498583, compound

Product 1

HCID 14852618Methyl 7-chloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylateYield 33.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice-cooled mixture of 30.5 g (0.15 mole) of 7-hydroxy-5-methoxycarbonyl-2-methyl-s-triazolo[1,5-a]pyrimidine and 300 ml of phosphorus oxychloride, 18.6 ml (0.15 ml) of N,N-dimethylaniline was added dropwise over 5 minutes and the mixture was stirred under reflux for 1 hour, followed by concentration. The residue obtained was dissolved in 300 ml of chloroform and washed with water, followed by drying over anhydrous magnesium sulfate. The solvent was evaporated and n-hexane was added to the set residue. The crystals were collected by filtration and dried to obtain 11.19 g of the title compound (Yield: 33.7%).

Workup

  1. additionwas added dropwise over 5 minutes
  2. temperatureunder reflux for 1 hour
  3. concentrationfollowed by concentration
  4. customThe residue obtained
  5. washwashed with water
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. additionn-hexane was added to the set residue
  9. filtrationThe crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-5815865ada8644ddbfa2a028c9e6654e
Source dataset
uspto-grants-1990_10
Patent number
US04966900

Reaction notes

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