5-Bromo-2-chloropyrimidine → 2-(Pyrimidin-2-yl)thio-5-bromopyrimidine

HRID 905227Notes

Reaction equation

HRID 905227 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[NH:9]1[CH:14]=[CH:13][CH:12]=[N:11][C:10]1=[S:15]>CC[O-].[Na+]>[N:9]1[CH:14]=[CH:13][CH:12]=[N:11][C:10]=1[S:15][C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 15504892-Mercaptopyrimidine

Product 1

HCID 204757282-(Pyrimidin-2-yl)thio-5-bromopyrimidineYield 35%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

2-Chloro-5-bromopyrimidine (10 mmol) was added to a solution of pyrimidine-2-thione (10 mmol) in ethanolic 0.24 M NaOEt (45 ml), the mixture heated under reflux for 2 hours, the solvent distilled off, the residue extracted with chloroform (70 ml), the chloroform solution shaken with 2 M NaOH and with water, the dried (MgSO4) solution evaporated and the residue repeatedly extracted with pet. ether leaving the title compound. Yield 35%, m.p. 178°-180° C. (iPrOH). 1H NMR (CDCl3): δ7.13 (H-5'), 8.60 (H-4', H-6'), 8.66 (H-4, H-6).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. distillationthe solvent distilled off
  4. extractionthe residue extracted with chloroform (70 ml)
  5. dry with materialthe dried (MgSO4) solution
  6. customevaporated
  7. extractionthe residue repeatedly extracted with pet. ether leaving the title compound

Sources & evidence

ORD record
ord-6bc53f52bfcd46c5aa26f84018d9bd1c
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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