Potassium Carbonate → Ethyl 2-(((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)methyl)-2-fluorobutanoate

HRID 1880936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880936
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH:12]1([NH:17][CH2:18][C:19]([F:27])([CH2:25][CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:17]([CH2:18][C:19]([F:27])([CH2:25][CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57955590Ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoate

Produkt 1

HCID 57955624Ethyl 2-(((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)methyl)-2-fluorobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a solution of 2,4-dichloro-5-nitropyrimidine (1.4 g, 7.2 mmol) in anhydrous acetone (50 ml) at 0° C., was added dropwise a solution of ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoate (1.38 g, 6 mmol) in acetone (10 mL) over 10 min. After which, potassium carbonate (2.5 g, 18 mmol) was added and the whole was stirred at rt for 18 h. After evaporation in vacuo, the residue was partitioned between ethyl acetate (200 ml) and water (200 ml). The organic layer was washed with NaHCO3, brine and water, dried over Na2SO4 and concentrated in vacuo to give a red residue which was used directly for next step (2.6 g). [M+H] calc'd for C16H22ClFN4O4, 389; found 389.

Aufarbeitung

  1. customAfter evaporation in vacuo
  2. customthe residue was partitioned between ethyl acetate (200 ml) and water (200 ml)
  3. washThe organic layer was washed with NaHCO3, brine and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a red residue which

Quellen und Nachweise

ORD-Eintrag
ord-6d68925854a24d468af22ea967c2bdf9
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318727B2

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