Iodine → Methyl 5-iodo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

HRID 245276Notes

Reaction equation

HRID 245276 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1.II.[I:15](O)(=O)(=O)=O>CO>[CH3:12][O:11][C:1]([C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[C:3]=1[I:15])=[O:10]

Participants

5

Reactant 3

HCID 807IodineHCID 65185Metaperiodic acidHCID 80257Orotic acid methyl ester

Product 1

HCID 45588307Methyl 5-iodo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylateYield 546.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl orotate (20.0 g, 118 mmol) was combined with iodine (12.8 g, 50 mmol) and periodic acid (4.8 g, 21 mmol) in methanol (250 mL) and heated at reflux for 20 h. After cooling to ambient temperature, the volatiles were removed by rotary evaporation. The solid residue was slurried in water, collected by filtration, washed well with water and dried under vacuum at 70° C. to provide the title compound (34 g, 97% yield) as a solid. It was used without further purification. MS: m/z=296.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 h
  3. customthe volatiles were removed by rotary evaporation
  4. filtrationcollected by filtration
  5. washwashed well with water
  6. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-d82901b925f644c1ba68572d319df8df
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

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