Chlorotrimethylsilane → 10-methyl-10-(4-pyridylmethyl)-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 1290765Notes

Reaction equation

HRID 1290765 reaction equation
[CH3:1][CH:2]1[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[H-].[Na+].C[Si](C)(C)Cl.Cl.Cl[CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1>C(O)(=O)C.CN(C)C=O>[CH3:1][C:2]1([CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydride2×HCID 745704-(Chloromethyl)pyridinium chlorideHCID 1897544610-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 1891818610-methyl-10-(4-pyridylmethyl)-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-oneYield 27.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 0.48 g of 10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 25 ml of dimethylformamide and 0.33 g of 80% sodium hydride is added 0.3 ml of trimethylchlorosilane at a temperature in the region of 20° C. and under cover of argon. The stirring is continued for one hour, followed by the addition of 0.07 g of 80% sodium hydride and the stirring is continued for 30 minutes. 0.36 g of 4-chloromethylpyridine hydrochloride is then added and the stirring is continued for 20 minutes. 2 ml of acetic acid are added to the reaction mixture, which is poured into 150 ml of ice-water and concentrated on a rotary evaporator. The evaporation residue is treated with 200 ml of ethyl acetate and filtered, and the filtrate is evaporated. The yellow-orange paste obtained is purified by chromatography on a column of silica (30 g), eluting with a mixture of dichloromethane and methanol (95/5 by volume). After trituration in 40 ml of ethyl ether, filtration and drying at 60° C. under vacuum (1 mmHg; 0.13 kPa), 0.18 g of 10-methyl-10-(4-pyridylmethyl)-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: 73.15, H: 4.91, N: 17.06, O: 4.87, % found C: 73.2, H: 5.1, N: 17.0).

Workup

  1. waitthe stirring is continued for 30 minutes
  2. waitthe stirring is continued for 20 minutes
  3. concentrationconcentrated on a rotary evaporator
  4. additionThe evaporation residue is treated with 200 ml of ethyl acetate
  5. filtrationfiltered
  6. customthe filtrate is evaporated
  7. customThe yellow-orange paste obtained
  8. customis purified by chromatography on a column of silica (30 g)
  9. washeluting with a mixture of dichloromethane and methanol (95/5 by volume)
  10. filtrationAfter trituration in 40 ml of ethyl ether, filtration
  11. customdrying at 60° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-98efe3dd5e7e47508aeae0e38f1ccba3
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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