Ethyl 4-chloroacetoacetate → HCID 14207605, compound

HRID 1086172Notes

Reaction equation

HRID 1086172 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH3:9])=[N:6][C:5]([Br:10])=[CH:4][N:3]=1.Cl[CH2:12][C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=O>CN(C)C=O>[Br:10][C:5]1[N:6]=[C:7]([NH:8][CH3:9])[C:2]2[N:3]([CH:12]=[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 121985205-Bromo-N~3~-methylpyrazine-2,3-diamine

Product 1

HCID 14207605HCID 14207605, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.03 g (10 mmol) of 2-amino-5-bromo-3-methylaminopyrazine are dissolved in 5 ml of dimethylformamide (DMF). A solution of 1.645 g(10 mmol) of ethyl (chloroacetyl)acetate in 5 ml of DMF is added dropwise with stirring. The mixture is maintained with stirring and under gentle reflux for 3 hours. The DMF is then evaporated off under reduced pressure and the residue, dissolved in 50 ml of anhydrous ethanol, is brought to reflux for one hour. After removal of the solvent, the residue is taken up with water, alkalinized and extracted with dichloromethane. After dehydration over anhydrous calcium chloride, the solvent is evaporated off under reduced pressure. The crude product is purified by chromatography on a silica column (eluant=dichloromethane to which 5% of methanol has been added). 0.4 g (Yld=30%) of ethyl 6-bromo-8-methylaminoimidazo[1,2-a]pyrazine-2-acetate (m.p. 104° C.) is obtained.

Workup

  1. temperatureThe mixture is maintained
  2. stirringwith stirring
  3. temperatureunder gentle reflux for 3 hours
  4. customThe DMF is then evaporated off under reduced pressure
  5. dissolutionthe residue, dissolved in 50 ml of anhydrous ethanol
  6. temperatureto reflux for one hour
  7. customAfter removal of the solvent
  8. extractionextracted with dichloromethane
  9. customAfter dehydration over anhydrous calcium chloride, the solvent is evaporated off under reduced pressure
  10. customThe crude product is purified by chromatography on a silica column (eluant=dichloromethane to which 5% of methanol has been added)

Sources & evidence

ORD record
ord-79cce7a7c39949959beb7fa26d3256e6
Source dataset
uspto-grants-1991_07
Patent number
US05028605

Reaction notes

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