Carbon Dioxide → HCID 77106010, compound

HRID 2201198Notes

Reaction equation

HRID 2201198 reaction equation
C([O-])=O.[NH4+].[CH3:5][N:6]1[C:11]2=[C:12]3[N:16]([C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:10]2[C:9](=[O:30])[N:8]([CH3:31])[C:7]1=[O:32])[CH2:15][CH:14]=[C:13]3[C:24]1[O:25][C:26]([CH3:29])=[CH:27][CH:28]=1.C(=O)=O.C(O)C>C(Cl)Cl.[Pd]>[CH3:5][N:6]1[C:11]2=[C:12]3[N:16]([C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:10]2[C:9](=[O:30])[N:8]([CH3:31])[C:7]1=[O:32])[CH2:15][CH2:14][CH:13]3[C:24]1[O:25][C:26]([CH3:29])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 702EthanolHCID 2723923Ammonium formateHCID 86723441HCID 86723441, compound

Product 1

HCID 77106010HCID 77106010, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ammonium formate (45.6 mg, 0.723 mmol), 1,3-dimethyl-9-(5-methylfuran-2-yl)-5-phenyl-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione (step 5) (27 mg, 0.072 mmol), and Pd/C (7.69 mg, 7.23 μmol) with a chip of dry ice was added ethanol (1446 μL). The reaction mixture was heated to 60° C. for 25 mins and allowed to stand at RT overnight. The reaction mixture was diluted with DCM and filtered through glass filter paper. The filtrate was washed with water and the organics collected and dried by passing through a phase separator cartridge. The organics were concentrated in vacuo. The crude product was loaded onto a 4 g silica cartridge and purified using an ISCO. The product was eluted with 0-80% EtOAc in iso-hexanes to afford the title compound;

Workup

  1. filtrationfiltered through glass
  2. filtrationfilter paper
  3. washThe filtrate was washed with water
  4. customthe organics collected
  5. customdried
  6. concentrationThe organics were concentrated in vacuo
  7. custompurified
  8. washThe product was eluted with 0-80% EtOAc in iso-hexanes

Sources & evidence

ORD record
ord-ef028cb91bca405fbfcecc46bc03fa8a
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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