Dimethylformamide → HCID 57927312, compound

HRID 889166Notes

Reaction equation

HRID 889166 reaction equation
[N:1]1[NH:2][C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[N:6][C:5]=12.[Br:11][CH2:12][CH2:13][CH2:14]Br.[H-].[Na+].CN(C)C=O>C(OCC)(=O)C.O>[Br:11][CH2:12][CH2:13][CH2:14][N:2]1[C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[N:6][C:5]2=[N:1]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80011,3-Dibromopropane2×HCID 24758Sodium hydride2×HCID 20551098[1,2,4]Triazolo[4,3-a]pyrimidin-3(2H)-one

Product 1

HCID 57927312HCID 57927312, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2H-[1,2,4]triazolo[4,3-a]pyrimidin-3-one (CAS 63206-77-9) (1.0 g), 1,3-dibromopropane (1.55 ml), sodium hydride (60% in oil) (353 mg) and N,N-dimethylformamide (20 ml) was stirred at room temperature for one day. After further addition of 1,3-dibromopropane (3.88 ml) and sodium hydride (60% in oil) (353 mg), stirring was continued at 80° C. for 2 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (190 mg).

Workup

  1. stirringstirring
  2. waitwas continued at 80° C. for 2 hours
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cfd4c2862fc64629ab7022e8bd10b725
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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