Chlorotrimethylsilane → HCID 18975456, compound

HRID 2393408Notes

Reaction equation

HRID 2393408 reaction equation
[H-].[Na+].[CH3:3][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.C[Si](C)(C)Cl.Cl.Cl[CH2:28][C:29]1[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=1>CN(C)C=O.O.C(O)(=O)C>[CH3:3][C:4]1([CH2:28][C:29]2[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=2)[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

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydride2×HCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 1897544610-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 18975456HCID 18975456, compoundYield 33.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.4 g of 80% sodium hydride is added over 5 minutes to a stirred solution, under an argon atmosphere, of 0.6 g of 10-methyl-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one in 30 ml of dimethylformamide. The stirring is continued for 10 minutes at a temperature in the region of 20° C., then 0.35 ml of trimethylchlorosilane is added and the stirring is continued for 10 minutes. 82 mg of sodium hydride are then added and the stirring is continued for 1 hour. 0.5 g of 2-chloromethyl-1-methylimidazole hydrochloride is then added and the stirring is continued for 2 hours. The reaction mixture is treated with 6 ml of acetic acid and 200 ml of water. The solution obtained is washed with ethyl acetate (2×200 ml) and the aqueous phase is concentrated on a rotary evaporator. The evaporation residue is triturated with 20 ml of isopropanol and filtered, and the filtrate is concentrated on a rotary evaporator. A pasty residue is obtained which is purified by chromatography on a column of silica (80 g), eluting with a dichloromethane/methanol mixture (85/15 by volume). 0.28 g of 10-methyl-10-[(l-methylimidazol-2-yl)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: 68.87, H: 5.17, N: 21.13, O: 4.83, % found C: 68.8, H: 5.2, N: 21.2).

Workup

  1. waitthe stirring is continued for 10 minutes
  2. waitthe stirring is continued for 1 hour
  3. waitthe stirring is continued for 2 hours
  4. customThe solution obtained
  5. washis washed with ethyl acetate (2×200 ml)
  6. concentrationthe aqueous phase is concentrated on a rotary evaporator
  7. customThe evaporation residue is triturated with 20 ml of isopropanol
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated on a rotary evaporator
  10. customA pasty residue is obtained which
  11. customis purified by chromatography on a column of silica (80 g)
  12. washeluting with a dichloromethane/methanol mixture (85/15 by volume)

Sources & evidence

ORD record
ord-99dc00a57b1543b78025faeda4bebd2e
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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