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

HRID 2377743Notes

Reaction equation

HRID 2377743 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 3h. 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-209048c6ca82441591d02030efb4e8b4
Source dataset
uspto-grants-2008_12
Patent number
US07470700B2

Reaction notes

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