2-Bromo-5-chloropyridine → 6-(5-Chloropyridin-2-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 241844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241844
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.CC(C)([O-])C.[Na+].[CH3:15][O:16][C:17]1[C:18]2[CH2:26][NH:25][CH2:24][CH2:23][C:19]=2[N:20]=[CH:21][N:22]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([N:25]2[CH2:24][CH2:23][C:19]3[N:20]=[CH:21][N:22]=[C:17]([O:16][CH3:15])[C:18]=3[CH2:26]2)=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 8170982-Bromo-5-chloropyridineHCID 23676156Sodium t-butoxideHCID 509892144-methoxy-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine

Produkt 1

HCID 668715086-(5-Chloropyridin-2-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

2-Bromo-5-chloropyridine (13.42 g, 0.067 mol), tris(dibenzylideneacetone)-dipalladium(0) (1.32 g, 1.43 mmol), sodium tert-butoxide (8.55 g, 0.088 mol), capped with a septum and purged with N2. A mixture of 4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (9.55 g, 0.0549 mol) in dry nitrogen-sparged toluene was added and the reaction mixture was sparged with nitrogen for an additional 30 min. The reaction mixture was then planced in an oil bath at 100° C., and heated overnight. After cooling, the mixture was diluted with ethyl acetate (180 mL), filtered and concentrated in vacuo. The residue was absorbed on 43 g silica, and purified on silica gel columned (0-60% EtOAc/hexane) to afford a light orange solid.

Aufarbeitung

  1. custompurged with N2
  2. customsparged toluene
  3. additionwas added
  4. customthe reaction mixture was sparged with nitrogen for an additional 30 min
  5. customThe reaction mixture was then planced in an oil bath at 100° C.
  6. temperatureheated overnight
  7. temperatureAfter cooling
  8. additionthe mixture was diluted with ethyl acetate (180 mL)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was absorbed on 43 g silica
  12. custompurified on silica gel
  13. customto afford a light orange solid

Quellen und Nachweise

ORD-Eintrag
ord-4e895c50189941ab81ca8f8bc53ec88f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653091B2

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