tert-butyl (3R)-3-aminopiperidine-1-carboxylate → (R)-tert-Butyl 3-(2-chloro-5-fluoro-6-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 573995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573995
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Cl:15][C:16]1[N:21]=[C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:19]([F:28])=[C:18](Cl)[N:17]=1>C(O)C>[Cl:15][C:16]1[N:17]=[C:18]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[C:19]([F:28])=[C:20]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[N:21]=1

Komponenten

4

Edukt 2

HCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 866441264-(2,6-Dichloro-5-fluoropyrimidin-4-yl)morpholine

Produkt 1

HCID 90409880(R)-tert-Butyl 3-(2-chloro-5-fluoro-6-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylateAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

(R)-tert-Butyl 3-aminopiperidine-1-carboxylate (1.60 g, 7.99 mmol) was added to a solution of 4-(2,6-dichloro-5-fluoropyrimidin-4-yl)morpholine (Preparation 11a, 1.01 g, 4.00 mmol) in ethanol (48 mL) and the resulting mixture was stirred and heated to reflux for 3 days. After cooling to ambient temperature, the solvent was evaporated under reduced pressure and the residue was partitioned between water and methylene chloride. The organic layer was separated, washed with water, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (0-100% ethyl acetate in hexanes) to give the title compound (0.810 g, 47%) as a white foam.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 3 days
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between water and methylene chloride
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated under reduced pressure
  9. customThe residue was purified by flash chromatography (0-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-481a68890fe54af89ae200b3fe852551
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034311B2

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