Alloxan → 5-(3-bromo-2-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione

HRID 1262940Notes

Reaction equation

HRID 1262940 reaction equation
C([Li])CCC.Br[C:7]1[O:8][CH:9]=[CH:10][C:11]=1[Br:12].[NH:13]1[C:21](=[O:22])[C:19](=O)[C:17](=[O:18])[NH:16][C:14]1=[O:15]>CCOCC.O1CCCC1>[Br:12][C:11]1[CH:10]=[CH:9][O:8][C:7]=1[CH:19]1[C:17](=[O:18])[NH:16][C:14](=[O:15])[NH:13][C:21]1=[O:22]

Participants

6

Reactant 3

HCID 5781AlloxanHCID 70215012,3-DibromofuranHCID 178418339Butyllithium

Product 1

HCID 204564765-(3-bromo-2-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

n-Butyl lithium is reacted with 2,3-dibromofuran in ether at -70° C. according to the procedure of Zaluski et al. [Bull. soc. chim. Fr., p. 1843 (1970)] and Sornay et al. [loc. cit., p. 990 (1971)]. The reaction mixture is warmed to -20° C. and an equivalent of anhydrous alloxan in tetrahydrofuran is added dropwise. Reaction is allowed to proceed to completion by warming to room temperature for 2 hours. The product, 5-(3-bromo-2-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione is isolated according to the method of Example 5.

Workup

  1. customReaction
  2. temperatureby warming to room temperature for 2 hours

Sources & evidence

ORD record
ord-ee2338c44d584f738f38a1872c542862
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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