Water → Pyrimidine-2,4,5-triol

HRID 36846

Reaction equation

HRID 36846 reaction equation
BrBr.[NH:3]1[CH:8]=[CH:7][C:6](=[O:9])[NH:5][C:4]1=[O:10].N1C=CC=NC=1.[OH2:17]>>[OH:17][C:7]1[C:6](=[O:9])[NH:5][C:4](=[O:10])[NH:3][CH:8]=1

Participants

5

Procedure

According to the synthetic method shown in Scheme A, above, bromine is added dropwise to an ice-cooled solution or suspension of a pyrimidine-2,4(1H,3H)-dione derivative of formula (III) in water until the solution or suspension is colored pale yellow. The pyrimidine-2,4(1H,3H)-dione derivatives of formula (III) are prepared, for example, by the methods described in Heterocyclic Compounds 16, The pyrimidine supplement II, D. J. Brown, An Interscience Publication, John Willy & Sons, New York, 1985, Table LVIII, page 728. To the resulting pale yellow solution or suspension is added carefully an ice cold saturated aqueous NaHCO3 solution. The resulting reaction mixture is refluxed, the solvent is removed and the residue is recrystallized from an appropriate solvent or chromatographed over silica-gel to give a 5-hydroxyprimidine-2,4(1H,3H)-dione derivative of formula (IV).

Workup

  1. temperaturecooled
  2. customThe resulting reaction mixture
  3. temperatureis refluxed
  4. customthe solvent is removed
  5. customthe residue is recrystallized from an appropriate solvent
  6. customchromatographed over silica-gel

Sources & evidence

ORD record
ord-dfa4a8f2f7244247bf8a9676065aef98
Source dataset
uspto-grants-1995_05
Patent number
US05418231

Linked notes

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