Ammonium Chloride → HCID 22024588, compound

HRID 501019Notes

Reaction equation

HRID 501019 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[O:19][CH3:20])=[N:9][CH:8]=[CH:7][N:6]2[C:21]=1[C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[CH3:2].[CH2:27]([Mg]Br)[CH2:28][CH3:29].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[O:19][CH3:20])=[N:9][CH:8]=[CH:7][N:6]2[C:21]=1[C:22]([OH:26])([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][CH3:25])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22024687HCID 22024687, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 22024588HCID 22024588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The resulting 1-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-1-butanone (220 mg, 0.63 mmol) was dissolved in tetrahydrofuran (2 mL), then a 0.90M propylmagnesium bromide solution in tetrahydrofuran (3.6 mL, 3.2 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temperature for 2 hours. An aqueous saturated ammonium chloride solution was added to the reaction mixture, which was extracted with ethyl acetate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=6:5) to give the title compound (150 mg) as white crystals.

Workup

  1. temperatureunder ice-cooling
  2. extractionwas extracted with ethyl acetate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=6:5)

Sources & evidence

ORD record
ord-a287209cd62e46ef95f9ecea1b12c944
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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