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

HRID 883534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883534
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>[O:12]=[C:11]1[NH:13][C:6]([C:5]([Br:3])=[O:15])=[CH:7][C:8](=[O:9])[NH:10]1

Komponenten

4

Edukt 2

HCID 967Orotic AcidHCID 68176Thionyl bromide3×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

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 45° C. over the course of about 80 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, 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl bromide (orotoyl bromide). This acyl bromide, 6.57 g (30 mmol), is put into a dry separatory funnel and combined with 25 mL of dry DCM for use in the next step of the reaction.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a196ce10701c4d49a57820538968a45c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236952B2

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