Dimethylformamide → HCID 18918183, compound

HRID 1290751Notes

Reaction equation

HRID 1290751 reaction equation
[CH3:1][CH:2]([CH3:21])[CH:3]=[C:4]1[C:16]2[N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13](=[O:20])[NH:12][C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2.CN(C)C=O.[H][H]>[Pd].CO>[CH2:3]([CH:4]1[C:16]2[N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13](=[O:20])[NH:12][C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2)[CH:2]([CH3:21])[CH3:1]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 70344114HCID 70344114, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18918183HCID 18918183, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.8 g of a mixture of 10-(2-methyl-1-propenyl)-5H,10H-imidazo[1,2-]indeno[1,2-e]pyrazin-4-one and 10-(2-methylpropylidene)-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one are hydrogenated in the presence of 180 ml of dimethylformamide, 20 ml of methanol and 0.5 g of 10% palladium on charcoal for 22 hours at 50° C. and at a pressure of 54 bar of hydrogen. After filtration of the catalyst under inert atmosphere, the solvents are evaporated off and the grey solid obtained (2.1 g) is purified by chromatography on a column of silica (180 g partially deactivated with 3 ml of water), using a mixture of dichloromethane and methanol (90/10 by volume) as eluent. After trituration in 20 ml of ethyl ether, filtration and drying at 100° C., 1.2 g of 10-isobutyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are thus obtained, in the form of a cream-coloured solid melting above 260° C. (Analysis % calculated C: 73.10, H: 6.13, N: 15.04, O: 5.73, % found C: 72.9, H: 5.6, N: 14.8).

Workup

  1. filtrationAfter filtration of the catalyst under inert atmosphere
  2. customthe solvents are evaporated off
  3. customthe grey solid obtained (2.1 g)
  4. customis purified by chromatography on a column of silica (180 g
  5. additiona mixture of dichloromethane and methanol (90/10 by volume) as eluent
  6. filtrationAfter trituration in 20 ml of ethyl ether, filtration
  7. customdrying at 100° C.

Sources & evidence

ORD record
ord-ab0d19bb31ef4189ad8baaa33a110cb8
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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