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

HRID 1262938Notes

Reaction equation

HRID 1262938 reaction equation
C([Li])CCC.Br[C:7]1[O:8][CH:9]=[C:10]([Br:12])[CH:11]=1.[NH:13]1[C:21](=[O:22])[C:19](=O)[C:17](=[O:18])[NH:16][C:14]1=[O:15]>CCOCC>[Br:12][C:10]1[CH:11]=[C:7]([CH:19]2[C:17](=[O:18])[NH:16][C:14](=[O:15])[NH:13][C:21]2=[O:22])[O:8][CH:9]=1

Participants

5

Reactant 3

HCID 5781AlloxanHCID 125723982,4-DibromofuranHCID 178418339Butyllithium

Product 1

HCID 204564795-(4-bromo-2-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-Butyl lithium is reacted with 2,4-dibromofuran in ether according to the procedure of Sornay et al. [Bull. soc. chim. Fr., p. 998 (1971)]. The resulting organolithium solution is reacted with alloxan at -60° to -65° C. according to Example 5, affording 5-(4-bromo-2-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione.

Sources & evidence

ORD record
ord-c20c0adc9c3c4317a5708bb572269377
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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