Bromine → 1-Methyl-2-methylthio-4-hydroxy-5-bromo-6-oxo-1,6-dihydro-pyrimidine

HRID 261790Notes

Reaction equation

[Br:1]Br.[CH3:3][N:4]1[C:9](=[O:10])[CH:8]=[C:7]([OH:11])[N:6]=[C:5]1[S:12][CH3:13]>[OH-].[Na+]>[CH3:3][N:4]1[C:9](=[O:10])[C:8]([Br:1])=[C:7]([OH:11])[N:6]=[C:5]1[S:12][CH3:13]

Participants

Conditions

Temperature: 5 °C

Procedure

16 g (0.1 mol) of bromine were added to a solution of 17.2 g (0.1 mol) of 1-methyl-2-methylthio-4-hydroxy-6-oxo-1,6-dihydro-pyrimidine in 110 ml of 1 N sodium hydroxide solution at room temperature. After the end of the addition, the batch was stirred for a further 0.5 hour and was then cooled to 5° C. The product which had precipitated was filtered off and rinsed with water. 18 g (76% of theory) of 1-methyl-2-methylthio-4-hydroxy-5-bromo-6-oxo-1,6-dihydro-pyrimidine were thus obtained in the form of pale yellow crystals of melting point 184° C. (with decomposition).

Workup

additionAfter the end of the addition
customThe product which had precipitated
filtrationwas filtered off
washrinsed with water

Sources & evidence

ORD record: ord-bea657cb27614936ab2fb5fb57c7f134
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04152426

Reaction notes

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