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Potassium Carbonate → 7-(2-(2-Bromoethoxy)ethoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline

HRID 547222
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 547222
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][Br:7].[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:29])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:26][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([NH:13][C:12]3[CH:27]=[CH:28][C:9]([Cl:8])=[CH:10][C:11]=3[F:29])=[N:15][CH:16]=[N:17]2)=[CH:22][C:21]=1[O:24][CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Produkt 1

HCID 187534287-(2-(2-Bromoethoxy)ethoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazolineAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

2-Bromoethyl ether (1.57 ml, 12 mmol) was added to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (1 g, 3.1 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (1.73 g, 12 mmol) in DMF (10 ml). The mixture was s for 18 hours at ambient temperature and was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and then brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/38/2). The purified product was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 7-(2-(2-bromoethoxy)ethoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (763 mg, 52%).

Aufarbeitung

  1. custom(prepared
  2. customfor 18 hours
  3. customat ambient temperature
  4. customwas partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialbrine, dried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/38/2)
  10. customThe purified product was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d9e46c9c96bc48529b84783ceb42e028
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE042353E1

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