Methyl iodide → 4,5-dihydro-3-(3-methoxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1607015Notes

Reaction equation

HRID 1607015 reaction equation
[OH-].[K+].[OH:3][C:4]([CH3:24])([CH3:23])[C:5]#[C:6][C:7]1[N:8]=[CH:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[N:13]([CH3:22])[CH2:12][C:11]=12.[CH3:25]I>CS(C)=O>[CH3:25][O:3][C:4]([CH3:24])([CH3:23])[C:5]#[C:6][C:7]1[N:8]=[CH:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[N:13]([CH3:22])[CH2:12][C:11]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 198515594,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515784,5-dihydro-3-(3-methoxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.58 g (80 mmol) of freshly powdered potassium hydroxide was suspended in 65 ml of dimethyl sulfoxide and cooled to 5°. 5.67 g (19.2 mmol) of 4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one and 5.47 g (38.5 mmol) of methyl iodide were added thereto in succession. The cooling bath was removed and the mixture was stirred for a further 1 hour. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with methylene chloride/methanol (19.5:0.5). After crystallization from tert.-butyl methyl ether there was obtained 4,5-dihydro-3-(3-methoxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 136°-137°.

Workup

  1. temperaturecooled to 5°
  2. customThe cooling bath was removed
  3. customThe reaction mixture was evaporated
  4. customthe residue was chromatographed on silica gel
  5. washwhile eluting with methylene chloride/methanol (19.5:0.5)
  6. customAfter crystallization from tert.-butyl methyl ether

Sources & evidence

ORD record
ord-580ac75aa10840c988cd23ddae87c10f
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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