N-bromobutanimide → HCID 67198034, compound

HRID 547388Notes

Reaction equation

HRID 547388 reaction equation
[C:1]([O:7][C:8]1[C:13](=[O:14])[N:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]2=[N:10][C:9]=1[C:19]([O:21][CH3:22])=[O:20])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1C(=O)N([Br:30])C(=O)C1>C(#N)C.C(O)(=O)C>[Br:30][C:16]1[CH:17]=[CH:18][C:11]2[N:12]([CH:15]=1)[C:13](=[O:14])[C:8]([O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[C:9]([C:19]([O:21][CH3:22])=[O:20])[N:10]=2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67198751HCID 67198751, compound

Product 1

HCID 67198034HCID 67198034, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl 3-[(pivaloyl)oxy]-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylate (see Example 1, Step 2a) and NBS (5 eqs.) were dissolved in a 3:1 mixture of acetonitrile and acetic acid. The solution was left standing at 5° C. with occasional shaking for 4 days. The solvents were removed under reduced pressure and the residue was suspended in chloroform. The precipitate was removed by filtration and the solution concentrated under vacuum. The residue was dissolved in dichloromethane, and triethylamine (7 eqs.) was added. The mixture was stirred for 1.5 hours at room temperature, the solvent removed under vacuum, and the residue partitioned between EtOAc and 1N aqueous HCl. The organic phase was washed with 1N aqueous HCl and the combined aqueous phases extracted with EtOAc. The combined organic phases were washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure. The product was isolated by flash chromatography (SiO2, eluant: PE/EtOAc, 4.5:5.5). The product was obtained as a light yellow solid.

Workup

  1. waitThe solution was left
  2. customstanding at 5° C.
  3. customThe solvents were removed under reduced pressure
  4. customThe precipitate was removed by filtration
  5. concentrationthe solution concentrated under vacuum
  6. dissolutionThe residue was dissolved in dichloromethane
  7. additiontriethylamine (7 eqs.) was added
  8. stirringThe mixture was stirred for 1.5 hours at room temperature
  9. customthe solvent removed under vacuum
  10. customthe residue partitioned between EtOAc and 1N aqueous HCl
  11. washThe organic phase was washed with 1N aqueous HCl
  12. extractionthe combined aqueous phases extracted with EtOAc
  13. washThe combined organic phases were washed with water
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure
  17. customThe product was isolated by flash chromatography (SiO2, eluant: PE/EtOAc, 4.5:5.5)
  18. customThe product was obtained as a light yellow solid

Sources & evidence

ORD record
ord-7ae6fa6b23c24b52b9d3042b6c0b14e6
Source dataset
uspto-grants-2011_05
Patent number
US07939537B2

Reaction notes

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