HCID 69805620, compound → HCID 9795553, compound

HRID 2184217Notes

Reaction equation

HRID 2184217 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][C:8]([CH:10]=[CH:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([O:18]CC2C=CC=CC=2)=[O:17])=[CH:14][CH:13]=1)=[O:9].[H][H]>C(O)(=O)C.[Pd]>[NH:3]1[CH2:4][CH2:5][CH2:6][N:1]=[C:2]1[NH:7][C:8]([CH2:10][CH2:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)=[O:9]

Participants

5

Reactant 2

HCID 69805620HCID 69805620, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9795553HCID 9795553, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

305 g (0.85 mol) of benzyl 4-(2-(pyrimidin-2-ylcarbamoyl)vinyl)benzoate were hydrogenated in a 20 l Būchi autoclave in 8 l of 20% aqueous acetic acid in the presence of 25 g of 10% palladium/charcoal at, 40° C. under a hydrogen pressure of 2 bar. After 6 h and uptake of 65.76 l of hydrogen the reaction was finished. After standing overnight the mixture was warmed to 70° C. and the catalyst filtered off. The autoclave was washed with 3 l of 20% aqueous acetic acid at 70° C. The catalyst was washed with 1.5 l of 20% aqueous acetic acid at 70° C. The filtrate was evaporated under reduced pressure in a rotary evaporator and the residue was dissolved in 1 l of water with heating. Upon cooling to room temperature the product precipitated. The mixture was cooled to 0° C. to 5° C., the product was filtered off, washed with cold water and dried under reduced pressure at 50° C. Yield: 212 g (90.6%).

Workup

  1. custom40° C.
  2. waitAfter standing overnight
  3. filtrationthe catalyst filtered off
  4. washThe autoclave was washed with 3 l of 20% aqueous acetic acid at 70° C
  5. washThe catalyst was washed with 1.5 l of 20% aqueous acetic acid at 70° C
  6. customThe filtrate was evaporated under reduced pressure in a rotary evaporator
  7. dissolutionthe residue was dissolved in 1 l of water
  8. temperaturewith heating
  9. temperatureUpon cooling to room temperature the product
  10. customprecipitated
  11. temperatureThe mixture was cooled to 0° C. to 5° C.
  12. filtrationthe product was filtered off
  13. washwashed with cold water
  14. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-fcb2fadb28224482976571f4fbd17513
Source dataset
uspto-grants-2005_05
Patent number
US06900318B1

Reaction notes

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