Sodium hydride → 3,4-dihydro-5-methyl-2-[1-(5-methyl-1H-imidazol-4-yl)ethyl]pyrimido[1,6-a]-indol-1(2H)-one

HRID 1657317Notes

Reaction equation

HRID 1657317 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:15])[NH:12][CH2:13][CH2:14][C:3]=12.[H-].[Na+].Cl.Cl[CH2:20][CH2:21][C:22]1[N:23]=[CH:24][NH:25][C:26]=1[CH3:27]>CN(C)C=O.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:15])[N:12]([CH:21]([C:22]3[N:23]=[CH:24][NH:25][C:26]=3[CH3:27])[CH3:20])[CH2:13][CH2:14][C:3]=12

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 10465394HCID 10465394, compoundHCID 124561924-(2-chloroethyl)-5-methyl-1H-imidazole hydrochloride

Product 1

HCID 98830773,4-dihydro-5-methyl-2-[1-(5-methyl-1H-imidazol-4-yl)ethyl]pyrimido[1,6-a]-indol-1(2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of 3,4-dihydro-5-methylpyrimido[1,6-a]-indol-1(2H)-one (1.88 g) in N,N-dimethylformamide (30 ml) was added sodium hydride (60% in mineral oil 1.12 g) at 5° C. After being stirred at 5° C. for 30 minutes, 4-(2-chloroethyl)-5-methyl-1H-imidazole hydrochloride (2.17 g) in N,N-dimethylformamide (30 ml) was added dropwise over 20 minutes. The mixture was stirred at 5° C. for 30 minutes and at ambient temperature for 16 hours. The reaction mixture was diluted with chilled water and extracted with a mixture of ethyl acetate and tetrahydrofuran (2:1, 30 ml×2). The organic layer was 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-methyl-1H-imidazol-4-yl)ethyl]pyrimido[1,6-a]indol-1(2H)-one as a powder.

Workup

  1. stirringThe mixture was stirred at 5° C. for 30 minutes and at ambient temperature for 16 hours
  2. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran (2:1, 30 ml×2)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (3%-methanol-chloroform)

Sources & evidence

ORD record
ord-893495ef6b9948ff8506616dfb8c8cda
Source dataset
uspto-grants-1993_10
Patent number
US05256780

Reaction notes

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