2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57982563, compound

HRID 1868451Notes

Reaction equation

HRID 1868451 reaction equation
[NH2:1][C:2]1[N:23]=[C:5]2[NH:6][C:7]([CH3:22])=[C:8]([C:18]([O:20][CH3:21])=[O:19])[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[N:4]2[N:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[NH2:1][C:2]1[N:23]=[C:5]2[N:6]=[C:7]([CH3:22])[C:8]([C:18]([O:20][CH3:21])=[O:19])=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 136393284HCID 136393284, compound

Product 1

HCID 57982563HCID 57982563, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of crude methyl 2-amino-7-(2,4-dichlorophenyl)-5-methyl-4,7-dihydro-[1,2,4]-triazolo[1,5-a]pyrimidine-6-carboxylate (10.1 mmol) in CH2Cl2 (100 mL) was added DDQ (2.75 g, 12.1 mmol). The reaction was kept at room temperature for 1 h and was quenched by satd aq NaHCO3 solution. The organic layer was washed with satd aq NaHCO3 and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded methyl 2-amino-7-(2,4-dichlorophenyl)-5-methyl-[1,2,4]-triazolo[1,5-a]pyrimidine-6-carboxylate (2.0 g, 56%) as a light yellow solid.

Workup

  1. customwas quenched by satd aq NaHCO3 solution
  2. washThe organic layer was washed with satd aq NaHCO3 and brine
  3. dry with materialto drying over anhydrous MgSO4
  4. filtrationFiltration, concentration
  5. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-0cc03a4dfd114dc087cc8889c888dce6
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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