Ethyl 4-chloroacetoacetate → HCID 14207605、化合物

HRID 1086172ノート

反応式

HRID 1086172 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 14207605HCID 14207605、化合物収率 30%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-79cce7a7c39949959beb7fa26d3256e6
出典データセット
uspto-grants-1991_07
特許番号
US05028605

反応ノート

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