HCID 22760701, compound → HCID 22760700, compound

HRID 1703795Notes

Reaction equation

HRID 1703795 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:16]=[CH:17][C:18]4[C:24](=[O:25])[C:23]([C:26]([OH:28])=[O:27])=[CH:22][N:21]([CH2:29][CH3:30])[C:19]=4[N:20]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:16]=[CH:17][C:18]4[C:24](=[O:25])[C:23]([C:26]([OH:28])=[O:27])=[CH:22][N:21]([CH2:29][CH3:30])[C:19]=4[N:20]=3)[CH2:11][CH2:10]2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 22760701HCID 22760701, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22760700HCID 22760700, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3.40 g of 2-[4-(p-nitrobenzyl)-1-piperazinyl]-8-ethyl-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid in 200 ml of acetic acid was hydrogenated over 0.55 g of 5% palladium-on-charcoal catalyst at room temperature until 3 mole equivalents of hydrogen were absorbed. The catalyst was removed by filtration and the filtrate was concentrated to dryness under reduced pressure. To the residue was added 30 ml of water and the resulting solution was neutralized with a saturated sodium bicarbonate solution. The crystalline precipitate was collected by filtration and dissolved with warming in 100 ml of ethanol. After removal of the insoluble material by filtration, the filtrate was kept under cooling to give the crude precipitated product (1.80 g), which was dissolved in a minimum amount of chloroform and chromatographed on 14 g of silica gel, using chloroform-methanol (a 50:1 ratio by volume) as eluent. Fractions containing the desired product were pooled and concentrated to dryness. The resulting solid was recrystallized from ethanol to give the pure product, m.p. 198°-201° C.

Workup

  1. customwere absorbed
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure
  4. additionTo the residue was added 30 ml of water
  5. filtrationThe crystalline precipitate was collected by filtration
  6. dissolutiondissolved
  7. temperaturewith warming in 100 ml of ethanol
  8. customAfter removal of the insoluble material
  9. filtrationby filtration
  10. temperatureunder cooling
  11. customto give the crude
  12. customprecipitated product (1.80 g), which
  13. dissolutionwas dissolved in a minimum amount of chloroform
  14. customchromatographed on 14 g of silica gel
  15. additionFractions containing the desired product
  16. concentrationconcentrated to dryness
  17. customThe resulting solid was recrystallized from ethanol
  18. customto give the pure product, m.p. 198°-201° C.

Sources & evidence

ORD record
ord-35ddefbc45724e50ac2f8509b7879070
Source dataset
uspto-grants-1978_11
Patent number
US04125615

Reaction notes

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