Bromine → 5-Bromo-2-(methylsulfanyl)pyrimidin-4(3H)-one

HRID 598081Notes

Reaction equation

HRID 598081 reaction equation
[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[Br:10]Br>C(O)(=O)C>[Br:10][C:6]1[C:7](=[O:9])[NH:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 798232-(Methylthio)-1H-pyrimidin-4-one

Product 1

HCID 2405655-Bromo-2-(methylsulfanyl)pyrimidin-4(3H)-oneYield 45.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution containing 2.0 g (14 mmol) of 2-(methylthio)pyrimidin-4(3H)-one in 10 ml of acetic acid under a nitrogen atmosphere was added 1.04 ml (14 mmol) of bromine in 2 ml acetic acid. The reaction was allowed to stir at room temperature for 30 min. The precipitated product was filtered, washed with acetic acid and suspended in hot acetic acid. To this suspension was added 0.2 ml bromine in 1 ml acetic acid. The product was collected, washed with acetic acid and recrystallized from ethanol to yield 1.4 g (45%) of product.

Workup

  1. filtrationThe precipitated product was filtered
  2. washwashed with acetic acid
  3. additionTo this suspension was added 0.2 ml bromine in 1 ml acetic acid
  4. customThe product was collected
  5. washwashed with acetic acid
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b4e8dd88e8b74127887858907dba5968
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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