Ammonia → HCID 86630669, compound

HRID 1851198Notes

Reaction equation

HRID 1851198 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=[C:4]2[N:3]=1.N>ClCCl.[Cl-].[Na+].O.[Zn]>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=[C:4]2[N:3]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 86630670HCID 86630670, compound

Product 1

HCID 86630669HCID 86630669, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6.00 g 5,7-dichloro-2-isopropyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine was dissolved in 360 mL dichloromethane. 360 mL brine, 120 mL ammonia solution 25% w/w and 6.00 g zinc powder were added and the mixture was stirred at room temperature for 3 h. The reaction mixture was filtered through Celite and was washed with dichloromethane and water. The organic phase was separated and the water phase was extracted with dichloromethane. The combined dichloromethane phases were dried over Na2SO4 and evaporated. The crude product contained 5,7-dichloro-2-isopropyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine. The crude product was dissolved again in dichloromethane. 360 mL brine, 120 mL ammonia solution 25% w/w and 6.00 g zinc powder were added and the mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through Celite and washed with dichloromethane and water. The organic phase was separated and the water phase was extracted with dichloromethane. The combined organic layers were dried over sodium sulphate and the solvent was evaporated. The product was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwas washed with dichloromethane and water
  3. customThe organic phase was separated
  4. extractionthe water phase was extracted with dichloromethane
  5. dry with materialThe combined dichloromethane phases were dried over Na2SO4
  6. customevaporated
  7. dissolutionThe crude product was dissolved again in dichloromethane
  8. addition360 mL brine, 120 mL ammonia solution 25% w/w and 6.00 g zinc powder were added
  9. stirringthe mixture was stirred at room temperature for 2 h
  10. filtrationThe reaction mixture was filtered through Celite
  11. washwashed with dichloromethane and water
  12. customThe organic phase was separated
  13. extractionthe water phase was extracted with dichloromethane
  14. dry with materialThe combined organic layers were dried over sodium sulphate
  15. customthe solvent was evaporated
  16. customThe product was used without further purification

Sources & evidence

ORD record
ord-70c34ff9653e4ccd9f2780053d1dd6a5
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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