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

HRID 1851158
Notes
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Reaction equation

HRID 1851158 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344DichloromethaneSolvent
HCID 57417360
Sodium chloride; water
Solvent

Procedure

34.5 g 5,7-dichloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine was dissolved in 500 mL dichloromethane. 500 mL brine, 250 mL 25% aqueous ammonia solution and 34.0 g zinc powder were added and the mixture was stirred at room temperature for 1 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 phase was dried over Na2SO4 and the solvent was evaporated. The crude product was purified by chromatography on silica gel (dichloromethane/ethyl acetate) to yield the desired compound.

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 phase was dried over Na2SO4
  6. customthe solvent was evaporated
  7. customThe crude product was purified by chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-2376b9504b974d679918bdaf0104af15
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957064B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes