2-Bromo-5-chloropyridine → HCID 66871508, compound

HRID 241844Notes

Reaction equation

HRID 241844 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 66871508HCID 66871508, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4e895c50189941ab81ca8f8bc53ec88f
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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