Sodium Acetate → HCID 13060219, compound

HRID 1982694Notes

Reaction equation

HRID 1982694 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]=[C:4]([NH:14][CH:15]=[O:16])[CH:3]=1.C([O-])(=O)C.[Na+]>C(O)C.[Pd]>[CH:15]([NH:14][C:4]1[CH:3]=[CH:2][N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]=1)=[O:16]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 23316850HCID 23316850, compound

Product 1

HCID 13060219HCID 13060219, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(6-chloro-4-formamidopyrimidin-2-yl)acetate (2.3 g.) and sodium acetate (0.93 g.) in 80% ethanol (50 ml.) was added 10% palladium on carbon (0.2 g.), and the mixture was stirred under a hydrogen atmosphere for 8 hours at ambient temperature. The reaction mixture was filtered and the filtrate was concentrated. To the residue were added ethyl acetate and a small amount of water and the ethyl acetate layer was separated. The remaining aqueous layer was extracted with ethyl acetate. The ethyl acetate layers were combined together, washed with water and dried over magnesium sulfate and then the solvent was distilled off. Thus obtained oily substance (2.2 g.) was purified by column chromatography on silica gel (40 g.) using a mixture of benzene and ethyl acetate as an eluent to give a pale brown solid of ethyl 2-(4-formamidopyrimidin-2-yl)acetate (1.3 g.), mp. 80° to 93° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionTo the residue were added ethyl acetate
  4. customa small amount of water and the ethyl acetate layer was separated
  5. extractionThe remaining aqueous layer was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThus obtained oily substance (2.2 g.) was purified by column chromatography on silica gel (40 g.)
  10. additiona mixture of benzene and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-1f25fb7a98904c34890a2f20c9772d51
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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