Bromine → HCID 178432679, compound

HRID 1501102Notes

Reaction equation

HRID 1501102 reaction equation
[Br:1]Br.[CH3:3][C:4]1[N:9]=[C:8]([OH:10])[CH:7]=[C:6]([CH3:11])[N:5]=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:7]1[C:8]([OH:10])=[N:9][C:4]([CH3:3])=[N:5][C:6]=1[CH3:11]

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 178429343HCID 178429343, compound

Product 1

HCID 178432679HCID 178432679, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

The solution of bromine (5.1 g, 31.9 mmol) in chloroform (30 mL) was added dropwise to the solution of 2,6-dimethylpyrimidin-4-ol (3.43 g, 27.6 mmol) in chloroform (50 mL) at 0° C. Then the mixture was stirred at 25° C. for 12 hours. Saturated sodium sulfite solution was added to the mixture until the colour of the mixture changed to colourless. The organic phase was separated, dried over sodium sulphate, filtered, and then concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give 5-bromo-2,6-dimethylpyrimidin-4-ol as a white solid (3.7 g, 66%). 1H NMR (300 MHz, d6-DMSO): δ 2.33 (s, 3H), 2.24 (s, 3H).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-4ca4a03953e746419904d371acec12a7
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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