Dimethylamine → 5-Chloro-N,N,2-trimethyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 1851225Notes

Reaction equation

HRID 1851225 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.[CH3:19][NH:20][CH3:21]>CN(C=O)C.O.ClCCl>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:20]([CH3:21])[CH3:19])[N:5]2[N:15]=[C:16]([CH3:18])[N:17]=[C:4]2[N:3]=1

Participants

6

Reactant 2

HCID 674DimethylamineHCID 866306805,7-Dichloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 866306975-Chloro-N,N,2-trimethyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 500 mg 5,7-dichloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine (prepared as described above) in 25 mL DMF were added 0.8 mL of a dimethylamine solution (60% in water). The mixture was stirred at room temperature for 45 minutes. The reaction mixture was diluted with water and dichloromethane. The phases were separated and the water layer was extracted with dichloromethane. The combined organic layers were dried over Na2SO4 and the solvent was removed by evaporation. The residue was suspended in diethylether and stirred for 5 hours. The desired product was filtered, dried and was used without further purification for the next step.

Workup

  1. customThe phases were separated
  2. extractionthe water layer was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent was removed by evaporation
  5. stirringstirred for 5 hours
  6. filtrationThe desired product was filtered
  7. customdried
  8. customwas used without further purification for the next step

Sources & evidence

ORD record
ord-4234f3b3989147edbc14156addcf3d16
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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