Tetrahydrofuran → HCID 18932910, compound

HRID 1656505Notes

Reaction equation

HRID 1656505 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])=[CH:7][N:6]=[C:5]1C1C=CC=CC=1)[CH:2]=[CH2:3].C[N+]1([O-])[CH2:34][CH2:33]OCC1.S([O-])([O-])(=O)=S.[Na+].[Na+].I([O-])(=O)(=O)=[O:44].[Na+].O1C[CH2:52][CH2:51][CH2:50]1>O.C(OCC)(=O)C.C(O)C.[Os](=O)(=O)(=O)=O>[CH2:15]([O:14][C:12]([NH:11][C:8]1[C:9](=[O:10])[N:4]([C:1](=[O:44])[CH2:2][C:3]2[CH:34]=[CH:33][CH:52]=[CH:51][CH:50]=2)[CH:5]=[N:6][CH:7]=1)=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

10

Reactant 5

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxide2×HCID 18932925HCID 18932925, compoundHCID 23667635Sodium periodate

Product 1

HCID 18932910HCID 18932910, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-allyl-5-benzyloxycarbonylamino-2-phenylpyrimid-6(1H)-one in tetrahydrofuran (200 mL) and water (30 mL) was added N-methylmorpholine-N-oxide (9.82 g) and osmium tetroxide (4.4 mL, 4% in water). The resulting solution was allowed to stir overnight. N-Methylmorpholine-N-oxide (1.65 g) was added and the solution was allowed to stir for 4 h. Sodium thiosulfate (saturated aqueous solution, 10 mL) and diatomoaceous earth (30 g) were added and the mixture was stirred for 0.5 h. The mixture was filtered and evaporated to give an oil. This oil was dissolved in ethyl acetate, washed (saturated aqueous sodium thiosulfate solution, 1N hydrochloric acid, brine), and evaporated to give an oil. This oil was dissolved in ethanol (230 mL) and a solution of sodium periodate (27 g) in water (40 mL) was added. The mixture was stirred for 2 h, filtered through diatomaceous earth and evaporated. The residue was dissolved in ethyl acetate and the solution was washed with water, dried, and evaporated to provide 5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinylacetaldehyde (25 g) as a white solid; TLC: ethyl acetate:diethyl ether (1:1), Rf =0.8.

Workup

  1. stirringto stir for 4 h
  2. stirringthe mixture was stirred for 0.5 h
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. customto give an oil
  6. washwashed (saturated aqueous sodium thiosulfate solution, 1N hydrochloric acid, brine)
  7. customevaporated
  8. customto give an oil
  9. stirringThe mixture was stirred for 2 h
  10. filtrationfiltered through diatomaceous earth
  11. customevaporated
  12. dissolutionThe residue was dissolved in ethyl acetate
  13. washthe solution was washed with water
  14. customdried
  15. customevaporated

Sources & evidence

ORD record
ord-3cc1940aeb284d73899917e0ece0ee66
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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