5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one → 7,8-bis(4-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271440Notes

Reaction equation

HRID 271440 reaction equation
Cl[C:2]1[N:7]2[C:8](=[O:11])[NH:9][N:10]=[C:6]2[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[N:3]=1.[Cl-].[CH3:27][Zn+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:4]2[N:3]=[C:2]([CH3:27])[N:7]3[C:8](=[O:11])[NH:9][N:10]=[C:6]3[C:5]=2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 587728405-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-oneHCID 178477797HCID 178477797, compound

Product 1

HCID 587728427,8-bis(4-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (50 mg, 0.128 mmol) and tetrakis(triphenylphosphine)palladium (7 mg, 0.006 mmol) in THF (0.5 mL) at room temperature under argon was added 2.0 M methylzinc chloride solution in THF (0.25 mL, 0.5 mmol). The reaction mixture was stirred at reflux for 1.5 h. The reaction mixture was cooled in an ice bath and quenched with saturated aqueous NH4Cl. EtOAc (5 mL) and water (5 mL) were added and the layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluted with 40% EtOAc-hexanes to obtain 40 mg of the title compound as a white solid. HPLC/MS: retention time=3.883 min, [M+H]30 =371.

Workup

  1. temperatureat reflux for 1.5 h
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customquenched with saturated aqueous NH4Cl
  4. additionEtOAc (5 mL) and water (5 mL) were added
  5. customthe layers were separated
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography
  10. washeluted with 40% EtOAc-hexanes

Sources & evidence

ORD record
ord-93342db745494e6db3c2ce7241760bb2
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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