HCID 19813705, compound → HCID 19813702, compound

HRID 467251Notes

Reaction equation

HRID 467251 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]3[CH2:14][C:15](=O)[N:16]([CH3:18])[CH2:17][C:12]3=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]3[CH:14]=[CH:15][N:16]([CH3:18])[CH2:17][C:12]3=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 19813705HCID 19813705, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19813702HCID 19813702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-(3-Methoxyphenyl)-7-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-6-one (65 mg) and 1N lithium aluminum hydride in tetrahydrofuran (2 mL) in tetrahydrofuran (4 mL) was kept at room temperature for 45 min. After quenching the reaction with 2N sodium hydroxide the reaction was filtered through celite and the solvent was removed in vacuo. The residue was subjected to flash chromatography on silica gel with 5% methanol in chloroform as the eluent to afford 3-(3-Methoxyphenyl)-7-methyl-7,8-dihydro-imidazo[1,5-a]pyrazine followed by 3-(3-Methoxyphenyl)-7-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine whose mono fumarate salt (Compound 32) was crystallized from ethanol/ether and melted at 211°-214°.

Workup

  1. customAfter quenching
  2. customthe reaction with 2N sodium hydroxide the reaction
  3. filtrationwas filtered through celite
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-35ed4105236f43d8af2dd4e05ca5bf0b
Source dataset
uspto-grants-1992_10
Patent number
US05159083

Reaction notes

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