4-[(2-Methoxyethoxy)methoxy]aniline → 5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamine

HRID 2274247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2274247
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:5]([F:18])=[CH:4][N:3]=1.[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.CCCCCC.C(OCC)(=O)C>C(O)C.C(O)(=O)C>[F:18][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[N:7][C:2]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([O:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH3:19])=[CH:27][CH:28]=2)=[N:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 131356894-[(2-Methoxyethoxy)methoxy]anilineHCID 21226206Ethyl acetate hexaneHCID 591746392-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine

Produkt 1

HCID 867243285-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamineAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of 2-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine (0.400 g) and 4-[(2-methoxyethoxy)methoxy]aniline (0.458 g), in ethanol (20 mL), was added acetic acid (4.65 mg). The reaction mixture was heated to reflux for 24 hr. Completion of reaction was monitored by TLC using hexane:ethyl acetate (8:2) as mobile phase. After completion of the reaction, ethanol was removed under reduced pressure at 40° C. To the residue water (25 mL) was added and mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and distilled under reduced pressure to give 0.4 g of 5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamine as a solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hr
  3. customCompletion of reaction
  4. customwas removed under reduced pressure at 40° C
  5. additionTo the residue water (25 mL) was added
  6. extractionmixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. distillationdistilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ad504a34985d43beac04d8cd4c8d0dfa
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126950B2

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