Hydrogen Bromide → HCID 70004542, compound

HRID 580902Notes

Reaction equation

HRID 580902 reaction equation
Br.[Br:2][CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]2=[N:7][C:6]=1[CH3:17].Br>CO.[Pd]>[Br:2][CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH2:12][CH2:13][CH2:14][CH:15]([OH:16])[C:8]2=[N:7][C:6]=1[CH3:17]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 70004170HCID 70004170, compound

Product 1

HCID 70004542HCID 70004542, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate 15 (55 g) and hydrobromic acid (48%) (55 g) in methanol (700 ml) was hydrogenated with palladium on activated carbon (10%) (5 g) as a catalyst. After completion, the precipitate was filtered off and the filtrate evaporated. Ammonium hydroxide was added to the residue which was subsequently extracted with CHCl3. The separated organic layer was dried and evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3 /CH3OH 90/10). The pure fractions were collected, the solvent was evaporated and the residue was recrystallized from 4-methyl-2-pentanone, yielding 17 g (44%) of (±)-6,7,8,9-tetrahydro-3-(2-bromoethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (intermediate 16).

Workup

  1. filtrationAfter completion, the precipitate was filtered off
  2. customthe filtrate evaporated
  3. additionAmmonium hydroxide was added to the residue which
  4. extractionwas subsequently extracted with CHCl3
  5. customThe separated organic layer was dried
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3 /CH3OH 90/10)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customthe residue was recrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-01d55b390ad14d72ae1b0c5a54fde133
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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