Ammonium formate → HCID 77105603, compound

HRID 2201177Notes

Reaction equation

HRID 2201177 reaction equation
[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:6]2[C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29])[CH2:12][CH2:11][CH:10]=[C:9]3[C:21]1[O:22][C:23]([CH3:26])=[CH:24][CH:25]=1.C([O-])=O.[NH4+]>[Pd].CCO>[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:6]2[C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29])[CH2:12][CH2:11][CH2:10][CH:9]3[C:21]1[O:22][C:23]([CH3:26])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86723420HCID 86723420, compound

Product 1

HCID 77105603HCID 77105603, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1,3-Dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (step 1) (411 mg, 1.061 mmol), 10% wt. palladium on activated carbon (113 mg, 0.106 mmol) and ammonium formate (669 mg, 10.61 mmol) were suspended in EtOH (30 mL) and the mixture stirred at 50° C. for 1 h. A further portion of 10% wt. palladium on activated carbon (113 mg, 0.106 mmol) was added and heating continued at 50° C. for a further 1 hour. The reaction mixture was cooled to RT and filtered through a Celite® (filter material) cartridge (10 g), rinsing the residue with MeOH. The filtrates were evaporated under reduced pressure. The residue was taken up in a small volume of MeOH and solids precipitated by addition of diethyl ether. The salts were removed by filtration and rinsing with diethyl ether. The solvent was evaporated and the residue was purified by chromatography on silica, eluting with 20% EtOAc in iso-hexane. Precipitation from EtOAc/iso-hexane afforded the title compound as a white solid.

Workup

  1. temperatureheating
  2. waitcontinued at 50° C. for a further 1 hour
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered through a Celite® (filter material) cartridge (10 g)
  5. washrinsing the residue with MeOH
  6. customThe filtrates were evaporated under reduced pressure
  7. customprecipitated by addition of diethyl ether
  8. customThe salts were removed by filtration
  9. washrinsing with diethyl ether
  10. customThe solvent was evaporated
  11. customthe residue was purified by chromatography on silica
  12. washeluting with 20% EtOAc in iso-hexane
  13. customPrecipitation from EtOAc/iso-hexane

Sources & evidence

ORD record
ord-a7ffbfbe49bb4d1ea25f4a5c4a1c1cd8
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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