Water → HCID 22024574, compound

HRID 500988Notes

Reaction equation

HRID 500988 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:13]([OH:17])[CH2:14][CH2:15][CH3:16])=[C:9]([CH2:11][CH3:12])[N:10]=2)[CH:5]=[CH:6][N:7]=1.I[CH2:19][CH3:20].[H-].[Na+].O>CN(C)C=O>[CH2:19]([O:17][CH:13]([C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]2=[N:10][C:9]=1[CH2:11][CH3:12])[CH2:14][CH2:15][CH3:16])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22024596HCID 22024596, compound

Product 1

HCID 22024574HCID 22024574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The resulting 1-(8-chloro-2-ethylimidazo[1,2-a]pyrazin-3-yl)-1-butanol was dissolved in N,N-dimethylformamide (2.2 mL), then iodoethane (0.079 mL, 0.99 mmol) and sodium hydride (65% in oil; 49 mg, 1.32 mmol) were added thereto under ice-cooling, and the mixture was stirred for 3 hours. Water 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=1:3) to give the title compound (55 mg) as a colorless oil.

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=1:3)

Sources & evidence

ORD record
ord-faf5de388ee04d27a797e34b996d95b6
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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