Sodium Hydroxide → 7-Chloro[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1036164Notes

Reaction equation

HRID 1036164 reaction equation
[N:1]1[N:5]2[C:6](O)=[CH:7][CH:8]=[N:9][C:4]2=[N:3][CH:2]=1.P(Cl)(Cl)([Cl:13])=O.[OH-].[Na+]>>[Cl:13][C:6]1[N:5]2[N:1]=[CH:2][N:3]=[C:4]2[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178516466HCID 178516466, compound

Product 1

HCID 217666127-Chloro[1,2,4]triazolo[1,5-a]pyrimidine

Procedure

5.4 g of [1,2,4]triazolo[1,5-a]pyrimidin-7-ol from the first synthesis step are introduced into 20 ml of phosphorus oxychloride with vigorous stirring. After completion, the mixture is warmed under reflux for a further 1.5 h. For work-up, the cooled batch is stirred in portions into 100 ml of ice-water and subsequently adjusted to pH 12 using conc. NaOH solution. The aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, and the solvent is removed in vacuo. The 7-chloro-[1,2,4]triazolo[1,5-a]pyrimidine obtained is employed in the following reaction without further purification; m.p. 190° [lit. 186-187° C.];

Workup

  1. temperatureAfter completion, the mixture is warmed
  2. temperatureunder reflux for a further 1.5 h
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-73d827e353994165b4d71a6722d8f7d6
Source dataset
uspto-grants-2013_10
Patent number
US08546406B2

Reaction notes

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