3-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione → 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

HRID 865634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865634
[Cl:1][C:2]1[C:7]([O:8]CC2C=CC=CC=2)=[CH:6][C:5]([N:16]2[C:21](=[O:22])[N:20]=[C:19]([N:23]([CH3:25])[CH3:24])[N:18]([CH3:26])[C:17]2=[O:27])=[C:4]([F:28])[CH:3]=1.[H][H]>[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:16]2[C:21](=[O:22])[N:20]=[C:19]([N:23]([CH3:24])[CH3:25])[N:18]([CH3:26])[C:17]2=[O:27])=[C:4]([F:28])[CH:3]=1

Komponenten

5

Edukt 2

HCID 199752643-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 199752573-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dioneAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4.62 g (11.4 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione and 460 mg of 10% palladium on charcoal in 50 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 14 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel eluting with a 1:1 v:v mixture of ethyl acetate and hexane to give 3.2 g of the title compound as a pale grey solid, m.p.: 247°-249° C. (dec); 1 -NMR (DMSO-d6) ppm 7.45 (d, 1H), 6.95 (d, 1H), 3.3 (s, 3H), 3.0 (s, 6H).

Aufarbeitung

  1. filtrationIt was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resultant crude product flash chromatographed over silica gel eluting with a 1:1 v
  5. additionv mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-b1b9f9daee894c8f84393cde620c3dde
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05567670

Notizen zur Reaktion

Wird geladen…