1,4-Dibromobenzene → 4-(4-Bromophenyl)-2-(methylthio)pyrimidine

HRID 1434982Notes

Reaction equation

HRID 1434982 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([Sn](CCCC)(CCCC)CCCC)[CH:6]=[CH:5][N:4]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=1>C1(C)C(C)=CC=CC=1.Cl[Pd]Cl>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 78041,4-DibromobenzeneHCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidine

Product 1

HCID 579362944-(4-Bromophenyl)-2-(methylthio)pyrimidine

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 7237O-XyleneSolvent

Procedure

2-Methylthio-4-tributylstannylpyrimidine (3.5 g, 7.5 mmol), PdCl2 (525 mg, 0.75 mmol) and 1,4-dibromobenzene (5.3 g, 22.5 mmol) were refluxed in xylene (75 ml) for 30 minutes, filtered and poured directly on a column of silicagel. Chromatography (acetone/hexanes:3/97 to 5/95) gave the title compound as white solid, which was crystallized from hexanes. Yield: 1.1 g (52%).

Workup

  1. filtrationfiltered
  2. additionpoured directly on a column of silicagel

Sources & evidence

ORD record
ord-4904a83d9480474791b47579f2f87159
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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