Potassium Carbonate → Ethyl 3-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)-2-fluoro-2-methylpropanoate

HRID 1880916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880916
[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:26])([CH3:25])[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]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:18][C:19]([F:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[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 57955537Ethyl 3-(cyclopentylamino)-2-fluoro-2-methylpropanoate

Produkt 1

HCID 57955550Ethyl 3-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)-2-fluoro-2-methylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a solution of 2,4-dichloro-5-nitropyrimidine (2.14 g, 11.0 mmol) in anhydrous acetone (30 ml) at 0° C., was added dropwise a solution of compound ethyl 3-(cyclopentylamino)-2-fluoro-2-methylpropanoate (2 g, 9.22 mmol) in acetone (10 mL) over 10 min. After which, potassium carbonate (3.8 g, 27.7 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. [M+H] calc'd for C15H20ClFN4O4, 375; found 375.

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-b583808e9add45929a1020063918f517
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318727B2

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