Orotic Acid → 6-(Chloromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 461646

Reaction equation

HRID 461646 reaction equation
[C:1](O)(=O)[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1.C=C1OC(=O)C1.ClCl.[Cl:20]CC(=O)CC(Cl)=O.NC(N)=O>>[Cl:20][CH2:1][C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1

Participants

6

Reactant 5

HCID 967Orotic AcidHCID 1176UreaHCID 12661DiketeneHCID 24526ChlorineHCID 30162624-Chloro-3-oxobutyryl chloride2×

Product 1

HCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedione

Procedure

German OS No. 2,025,247 teaches that orotic acid can be prepared by converting, in a first stage, diketene and chlorine to γ-chloroacetoacetic acid chloride, in a second stage, reacting the γ-chloroacetoacetic acid chloride with urea to form 6-chloromethyluracil, separating the 6-chloromethyluracil and oxidizing the 6-chloromethyluracil with hydrogen peroxide to orotic acid.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-1880da1d0333470ab4ae01d8c2a3dee2
Source dataset
uspto-grants-1977_12
Patent number
US04064126

Linked notes

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