Methyl iodide → 3,4-dihydro-5-methyl-2-[(1,5-dimethylimidazol-4-yl)methyl]pyrimido[1,6-a]indol-1(2H)-one

HRID 1657319Notes

Reaction equation

HRID 1657319 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:22])[N:12]([CH2:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:13][CH2:14][C:3]=12.[H-].[Na+].[CH3:25]I>CN(C)C=O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:22])[N:12]([CH2:15][C:16]3[N:17]=[CH:18][N:19]([CH3:25])[C:20]=3[CH3:21])[CH2:13][CH2:14][C:3]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 103346343,4-dihydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)-methyl]pyrimido[1,6-a]indol-1(2H)-one

Product 1

HCID 104479943,4-dihydro-5-methyl-2-[(1,5-dimethylimidazol-4-yl)methyl]pyrimido[1,6-a]indol-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3,4-dihydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]pyrimido[1,6-a]indol-1(2H)-one (343 mg) in N,N-dimethylformamide (20 ml) was added sodium hydride (60% in mineral oil, 51.3 mg) at 5° C. and the mixture was stirred at the same temperature for 30 minutes. Methyl iodide (182 mg) in N,N-dimethylformamide (10 ml) was added dropwise to the solution at 50° C. during 2 hours. After 30 minutes of stirring at the same temperature, the reaction mixture was evaporated in vacuo. The residue was diluted with a mixture of tetrahydrofuran and ethyl acetate (1:3, 20 ml), washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (3% -methanol-chloroform) to give 3,4-dihydro-5-methyl-2-[(1,5-dimethylimidazol-4-yl)methyl]pyrimido[1,6-a]indol-1(2H)-one as crystal. The crystal was dissolved with 2N-hydrochloric acid (2 ml) and evaporated in vacuo. The crystalline residue was washed with acetone to give 3,4-dihydro-5-methyl-2-[(1,5-dimethylimidazol-4-yl)methyl]pyrimido[1,6-a]indol-1-(2H)one hydrochloride (0.2 g).

Workup

  1. stirringAfter 30 minutes of stirring at the same temperature
  2. customthe reaction mixture was evaporated in vacuo
  3. additionThe residue was diluted with a mixture of tetrahydrofuran and ethyl acetate (1:3, 20 ml)
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (3% -methanol-chloroform)

Sources & evidence

ORD record
ord-ccb45128317b419999363c2ba9a33c27
Source dataset
uspto-grants-1993_10
Patent number
US05256780

Reaction notes

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