Potassium Carbonate → HCID 57962416, Verbindung

HRID 541843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541843
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([F:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]3[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=[CH:12][N:11]=3)[CH:5]=[CH:6][CH:7]=2)[C:28]([F:32])=[CH:27][N:26]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 57962008tert-Butyl {2-[2-(3-aminophenyl)ethyl]pyridin-4-yl}carbamate

Produkt 1

HCID 57962416HCID 57962416, VerbindungAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl {2-[2-(3-aminophenyl)ethyl]pyridin-4-yl}carbamate (240 mg, 0.76 mmol) and 2,4-dichloro-5-fluoropyrimidine (134 mg, 0.80 mmol) in N,N-dimethylformamide (3.5 mL) was added potassium carbonate (318 mg, 0.23 mmol). The resultant mixture was stirred overnight at room temperature. The reaction mixture was filtered first to remove K2CO3, followed by quenching with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine, then dried (Na2SO4), filtered and concentrated to give the residue, which was purified by silica gel column chromatography to give the desired product as an off-white solid (123 mg, 36%). LCMS for C22H24ClFN5O2 (M+H)+: m/z=444.1.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered first
  2. customto remove K2CO3
  3. customby quenching with water
  4. additionEtOAc was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc twice
  7. washThe combined organic layers were washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give the residue, which
  12. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-60a5c97cddfb4b7da123b8e42ab783f3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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