Ammonia → 5-Chloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1915573Notes

Reaction equation

HRID 1915573 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]([CH3:18])[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]([CH3:18])[N:17]=[C:4]2[N:3]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 866306805,7-Dichloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 772315025-Chloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

34.5 g 5,7-dichloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine is dissolved in 500 ml dichloromethane. 500 ml brine, 250 ml ammonia solution 25% w/w and 34.0 g zinc powder are added and the mixture is stirred at room temperature for 1 h. The reaction mixture is filtrated over kieselgur and is washed with dichloromethane and water. The organic phase is separated and the water phase is extracted with dichloromethane. The combined dichloromethane phase is dried over Na2SO4 and the solvent is evaporated. The crude product is purified by chromatography on silica gel (dichloromethane/ethyl acetate) to yield the desired compound.

Workup

  1. filtrationThe reaction mixture is filtrated over kieselgur
  2. washis washed with dichloromethane and water
  3. customThe organic phase is separated
  4. extractionthe water phase is extracted with dichloromethane
  5. dry with materialThe combined dichloromethane phase is dried over Na2SO4
  6. customthe solvent is evaporated
  7. customThe crude product is purified by chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-567db391c00c46e0abf87fde7be9ffbb
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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