Dimethylformamide → 10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
Reaction equation
O[CH:2]=[C:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2.CN(C)C=O>[Pd].CO>[CH3:2][CH:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2Participants
Procedure
10-Methyl-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one may be obtained in the following way: a mixture of 1 g of 10-hydroxymethylene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 80 ml of dimethylformamide and 20 ml of methanol is hydrogenated at a temperature in the region of 20° C. and at normal pressure for 4 hours in the presence of 10% palladium-on-charcoal. After filtration of the catalyst under an inert atmosphere, the solvents are evaporated off and the beige-coloured solid obtained (1.25 g) is purified by chromatography on a column of silica (100 g) with a mixture of dichloromethane and methanol (95/5 by volume). After drying at 90° C., 0.35 g of 10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained in the form of a cream-coloured solid melting above 260° C. (Analysis, % calculated C: 70.87, H: 4.67, N: 17.71, O: 6.74, % found C: 70.5, H: 4.4, N: 17.4).
Workup
- filtrationAfter filtration of the catalyst under an inert atmosphere
- customthe solvents are evaporated off
- customthe beige-coloured solid obtained (1.25 g)
- customis purified by chromatography on a column of silica (100 g) with a mixture of dichloromethane and methanol (95/5 by volume)
- customAfter drying at 90° C.
Sources & evidence
- ORD record
- ord-7cdc376bf2b148b8a7017137db7a64b8
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05807859
Reaction notes
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