5-Bromo-2-chloropyrimidine → 2-(Pyrimidin-2-yl)thio-5-bromopyrimidine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).