Methanol → HCID 69331847, compound

HRID 915035Notes

Reaction equation

HRID 915035 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[N:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](=[O:19])[N:15]([CH:20]([CH3:22])[CH3:21])[N:14]=2)=[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:8]=1)(=O)=O.[CH3:31][OH:32].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN([CH:65]=[O:66])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:20]([N:15]1[C:16](=[O:19])[CH:17]=[CH:18][C:13]([C:10]2[N:11]=[CH:12][C:7]([C:31]([O:66][CH3:65])=[O:32])=[N:8][C:9]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:14]1)([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 86600914HCID 86600914, compound

Product 1

HCID 69331847HCID 69331847, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2-pyrazinyl trifluoromethanesulfonate (1.0 g), MeOH (5.98 ml), palladium acetate (102 mg) and 1,3-bis(diphenylphosphino)propane (187 mg) in DMF (10 ml) was stirred with CO gas bubbling at 20° C. for 30 minutes. Then the reaction mixture was stirred under CO gas at 60° C. for 6 hours. Water and EtOAc were added to the reaction mixture. The organic layer was washed with 1N HCl, aq. NaHCO3 and brine. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain methyl 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2-pyrazinecarboxylate (68 mg) as white powder.

Workup

  1. custombubbling at 20° C. for 30 minutes
  2. stirringThen the reaction mixture was stirred under CO gas at 60° C. for 6 hours
  3. additionWater and EtOAc were added to the reaction mixture
  4. washThe organic layer was washed with 1N HCl, aq. NaHCO3 and brine
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluted with a mixture of n-hexane and EtOAc
  10. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-403e80e90d3242f18ff76d404557db36
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

Loading…