Hydrochloric Acid → 5-Bromo-2-chloropyrimidin-4-ol

HRID 2105309Notes

Reaction equation

HRID 2105309 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-:10].[Na+].Cl>C1COCC1>[Br:1][C:2]1[C:3](=[O:10])[NH:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 111601145-Bromo-2-chloropyrimidin-4-olYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2,4-dichloro-pyrimidine (5.0 g, 22 mmol) was stirred in THF (10 mL) with 1N NaOH (30 mL) at r.t. for 3 h. The solution was made slightly acidic with 1N HCl and was extracted with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo. Precipitation from 20% CHCl3/hexanes and collection by filtration gave 2.92 g (64%) of 5-bromo-2-chloro-3H-pyrimidin-4-one as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 13.33 (br s, 1H), 8.35 (s, 1H). MS (ES) [m+H] calc'd for C4H2N2OBrCl, 209, 211, 213; found 209, 211, 213.

Workup

  1. extractionwas extracted with CHCl3
  2. dry with materialOrganics were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPrecipitation
  5. customfrom 20% CHCl3/hexanes and collection
  6. filtrationby filtration

Sources & evidence

ORD record
ord-0164122424c34c42bd5f494b05a7168d
Source dataset
uspto-grants-2009_08
Patent number
US07579357B2

Reaction notes

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