Water → 4-((5-Bromopyrimidin-2-yl)thio)aniline

HRID 736328Notes

Reaction equation

HRID 736328 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([S:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145104-AminothiophenolHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 27610434-((5-Bromopyrimidin-2-yl)thio)anilineYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-bromo-2-chloropyrimidine (5 g, 0.026 mol), 4-aminothiophenol (3.24 g, 0.026 mol), and K2CO3 (7.14 g, 0.052 mol) in dry DMSO (50 mL) was stirred at 120 ° C. for 2.5 hours under N2. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then dried. The solvent was evaporated to give a residue that was purified by silica gel flash column chromatography (ethyl acetate-hexane 1:3) to give 4-(5-bromopyrimidin-2-ylsulfanyl)phenylamine (4n), yield 74%. 1H NMR (400 MHz, CDCl3): δ 8.51 (s, 2H), 7.37 (d, J) 8.0 Hz, 2H), 6.72 (d, J) 8.0 Hz, 2H), 2.63 (s, 2H); EI-MS m/z 281 [M]+, 283 [M+2]+.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customdried
  5. customThe solvent was evaporated
  6. customto give a residue that
  7. customwas purified by silica gel flash column chromatography (ethyl acetate-hexane 1:3)

Sources & evidence

ORD record
ord-c77cc5fe8dd74ba0b3e322fd4156ed0f
Source dataset
uspto-grants-2009_09
Patent number
US07595326B2

Reaction notes

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