1,3-Bis(diphenylphosphino)propane → HCID 68676385, compound

HRID 2233038Notes

Reaction equation

HRID 2233038 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[CH:7]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CS(C)=O.C[CH2:52][O:53][C:54](C)=[O:55].O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:52][O:53][C:54]([C:2]1[N:3]=[C:4]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[CH:7]=1)=[O:55]

Participants

6

Reactant 4

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 22036561Dimethyl sulfoxide methanolHCID 22728543Water ethylacetateHCID 68675824HCID 68675824, compound

Product 1

HCID 68676385HCID 68676385, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
75 °C

Procedure

A solution of 521 mg of the product of Step E, 313 mg of 1,3-bis-(diphenylphosphino)propane, 212 mg of palladium(II) acetate and 13.8 g of TEA in a 10:1 mixture of MeOH/DMSO (209 mL) was agitated under a carbon monoxide atmosphere (45 psi) at 75° C. After 14 h, the reaction was cooled to ambient temperature and portioned between EtOAc/water. The resulting mixture was filtered through a pad of diatomaceous earth and the solids washed with EtOAc. The layers were separated and the aqueous was extracted with EtOAc. The combined organic extracts were washed with sat. sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated to provide 8-isopropylamino-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-6-carboxylic acid methyl ester as an oil. MS (M+H+)=252.3.

Workup

  1. temperaturethe reaction was cooled to ambient temperature
  2. filtrationThe resulting mixture was filtered through a pad of diatomaceous earth
  3. washthe solids washed with EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with EtOAc
  6. washThe combined organic extracts were washed with sat. sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-793c10f29b14465e878c6c72c3e7c92b
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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