Acetic Acid → HCID 58016851, compound

HRID 1926895Notes

Reaction equation

HRID 1926895 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH:10]([O:12][C:13]1[C:14]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[C:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:19][C:15]=2[N:16]=[CH:17][N:18]=1)[CH3:11])C1C=CC=CC=1.C(O)(=O)C>[Pd].CO>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:14]3[C:13]([O:12][CH:10]([CH3:11])[CH2:9][NH:8][CH3:1])=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 58016908HCID 58016908, compound

Product 1

HCID 58016851HCID 58016851, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Put 500 mg palladium on charcoal (10%) under argon in 100 ml methanol. Add 1.7 g (3.55 mmol) (+/−)-N-Benzyl-2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-N-methylpropane-1-amine and 2.5 ml acetic acid, and hydrogenate at RT and normal pressure. After 2 h filter with a diatomite filter and concentrate by evaporation. Dissolve the residue in water and wash twice with ethyl acetate. Discard the ethyl acetate phases. Make the aqueous phase basic with solid sodium hydrogencarbonate and extract twice with ethyl acetate. Wash the combined ethyl acetate phases once with satd. sodium chloride solution, dry over magnesium sulphate and concentrate by evaporation. 900 mg (65.2% of theor.) of the target compound is obtained.

Workup

  1. customhydrogenate at RT
  2. filtrationAfter 2 h filter with a diatomite
  3. filtrationfilter
  4. concentrationconcentrate by evaporation
  5. dissolutionDissolve the residue in water
  6. washwash twice with ethyl acetate
  7. extractionextract twice with ethyl acetate
  8. washWash the combined ethyl acetate phases once with satd
  9. dry with materialsodium chloride solution, dry over magnesium sulphate
  10. concentrationconcentrate by evaporation
  11. custom900 mg (65.2% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-51b82f57afb64de98025a515a0943ba3
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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