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

HRID 1646775Notes

Reaction equation

HRID 1646775 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:19][CH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>CN(C)C=O.O>[ClH:19].[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]([CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:13][CH2:14][C:3]=12

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 10465394HCID 10465394, compound

Product 1

HCID 197871203,4-dihydro-5-methyl-2-(4-pyridylmethyl)pyrimido[1,6-a]-indol-1(2H)-one hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3,4-dihydro-5-methylpyrimido[1,6-a]-indol-1(2H)-one (188 mg) in N,N-dimethylformamide (3 ml) was added sodium hydride (60% in mineral oil, 88 mg) at 5° C. The mixture was stirred at the same temperature for 20 minutes. A solution of 4-chloromethylpyridine hydrochloride in N,N-dimethylformamide (3 ml) was added dropwise at 5° C. over five minutes. The reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 3 hours. The reaction mixture was diluted with chilled water and extract two times with 5%-methanol-chloroform. The extract was washed twice with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was dissolved in 1N-hydrochloric acid (10 ml) and evaporated in vacuo. The residue was pulverized with acetone to give 3,4-dihydro-5-methyl-2-(4-pyridylmethyl)pyrimido[1,6-a]-indol-1(2H)-one hydrochloride (160 mg).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 3 hours
  2. extractionextract two times with 5%-methanol-chloroform
  3. washThe extract was washed twice with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in 1N-hydrochloric acid (10 ml)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-eb90867800504fe4a808dd4e8ba34e27
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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