Diethyl Ether → 5-hydroxy-5-(2-methoxy-3-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione

HRID 1262943Notes

Reaction equation

HRID 1262943 reaction equation
[CH3:1][O:2][C:3]1S[CH:5]=[CH:6][C:7]=1Br.C([Li])CCC.[NH:14]1[C:22](=[O:23])[C:20](=[O:21])[C:18](=[O:19])[NH:17][C:15]1=[O:16].CC[O:26]CC>O1CCCC1>[OH:21][C:20]1([C:7]2[CH:6]=[CH:5][O:26][C:3]=2[O:2][CH3:1])[C:18](=[O:19])[NH:17][C:15](=[O:16])[NH:14][C:22]1=[O:23]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5781AlloxanHCID 104651873-Bromo-2-methoxythiopheneHCID 178418339Butyllithium

Product 1

HCID 204564775-hydroxy-5-(2-methoxy-3-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxy-3-bromothiophene is reacted with n-butyl lithium in ether at 0° to 5° C., following the method of Sornay et al. [Bull. soc. chim. Fr. (3), p. 999 (1971)]. The organolithium reagent is cooled to -10° to -20° C. and reacted with an equivalent of alloxan in tetrahydrofuran. The reaction mixture is allowed to warm to room temperature and 5-hydroxy-5-(2-methoxy-3-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione isolated according to the method of Example 5.

Sources & evidence

ORD record
ord-38944e87c62b4640b5e86a3db3638aa8
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

Loading…