Sodium borohydride → 2-Chloro-6-(1-(4,6-dimethoxypyrimidin-2-yl)ethyl)aniline

HRID 1678043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678043
CS[C:3]([C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[NH2:12])[CH3:4].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:12][C:6]1[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=1[CH:3]([C:13]1[N:14]=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[N:18]=1)[CH3:4]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 58970390HCID 58970390, Verbindung

Produkt 1

HCID 589703892-Chloro-6-(1-(4,6-dimethoxypyrimidin-2-yl)ethyl)anilineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11791229Dichloronickel;hexahydrateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-{1-methylthio-1-(2-amino-3-chlorophenyl)ethyl}-4,6-dimethoxypyrimidine 3 g (8.8 mmol) in 100 ml methanol, nickel (II) chloride hexahydrate 4.2 g (17.7 mmol) was added at 0° C. and the mixture was stirred for 30 minutes. Then, at the same temperature, sodium borohydride 1.35 g (35 mmol) was added little by little thereto. The solution was stirred at room temperature for 1 hour and then the solvent was distilled off. 2N-hydrochloric acid was added to the residue and then 28% aqueous ammonia was added and the mixture was extracted with ethyl acetate. The organic layer washed with an aqueous solution of sodium hydroxide and the solvent was distilled off. After washing with hexane, the deposited crystals were filtered to obtain 2-{1-(2-amino-3-chlorophenyl)ethyl}-4,6-dimethoxypyrimidine 2.12 g (82%).

Aufarbeitung

  1. stirringThe solution was stirred at room temperature for 1 hour
  2. distillationthe solvent was distilled off
  3. addition2N-hydrochloric acid was added to the residue
  4. addition28% aqueous ammonia was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer washed with an aqueous solution of sodium hydroxide
  7. distillationthe solvent was distilled off
  8. washAfter washing with hexane
  9. filtrationthe deposited crystals were filtered

Quellen und Nachweise

ORD-Eintrag
ord-91078162961246a188fd8a238288884b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008484B2

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