Pyrimidine → Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoate

HRID 1044080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044080
[CH:1]1([NH:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1.N1C=CC=NC=1>CC(C)=O>[CH:1]1([N:6]([C:22]2[C:23]([N+:27]([O-:29])=[O:28])=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=2)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 9260PyrimidineHCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 28307099Methyl 3-(cyclopentylamino)propanoate

Produkt 1

HCID 57940528Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Methyl 3-(cyclopentylamino)propanoate (0.838 g, 0.005 mol, 1 eq) and K2CO3 (0.676 g, 0.005 mol, 1 eq) were added to acetone (5 mL) and the resulting mixture cooled to 0° C. before the dropwise addition of 2,4-dichloro-5-nitropyrimidine (1.04 g, 0.0055 mol, 1.1 eq). The reaction mixture (RM) was warmed to rt and stirring continued for an additional 16 h before the addition of a further 0.12 eq of the pyrimidine. Stirring continued for a further 3 h. The RM was evaporated under reduced pressure and the product extracted using EtOAc/H2O. The organic extracts were washed with sat NaCl, dried (MgSO4) and evaporated under reduced pressure to give the product as a brown oily residue (1.04 g, 65%); MS+ve: 329.2; Rt=3.78 min (Analytical—1).

Aufarbeitung

  1. stirringStirring
  2. customThe RM was evaporated under reduced pressure
  3. extractionthe product extracted
  4. washThe organic extracts were washed with sat NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d9745b90e26c4d0c96438cc52e1aa77f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563542B2

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