Orotic Acid → 2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl bromide

HRID 883538Notes

Reaction equation

HRID 883538 reaction equation
S(Br)([Br:3])=O.[C:5]([OH:15])(=O)[C:6]1[NH:13][C:11](=[O:12])[NH:10][C:8](=[O:9])[CH:7]=1>O>[C:5]([Br:3])(=[O:15])[C:6]1[NH:13][C:11](=[O:12])[NH:10][C:8](=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 967Orotic AcidHCID 68176Thionyl bromide3×

Product 1

HCID 461847302,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl bromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 10.07 ml (130 mmol) of thionyl bromide, and a water condenser, is placed 15.61 g (100 mmol) of orotic acid. Addition of the thionyl bromide is completed with heating to about 30° C. over the course of about 130 minutes. When addition of the thionyl bromide is complete the mixture is heated and stirred for an additional hour. The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled. The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl bromide, orotoyl bromide. This acyl bromide, 10.95 g (50 mmol), is put into a dry separatory funnel and combined with 100 mL of dry DCM for use in the next step of the reaction.

Workup

  1. customIn a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer
  2. customfixed with a separatory funnel
  3. temperatureis heated
  4. distillationthe crude mixture is distilled
  5. distillationThe crude distillate in the receiving flask is then fractionally distilled

Sources & evidence

ORD record
ord-65fe582f5e70446fbda47158f107ae81
Source dataset
uspto-grants-2012_08
Patent number
US08236952B2

Reaction notes

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