4-Iodo-2-(methylthio)pyrimidine → 4-(5-Bromothiophen-2-yl)-2-methylsulfanylpyrimidine

HRID 1434918Notes

Reaction equation

HRID 1434918 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[Br:10][C:11]1[S:15][C:14]([Sn](CCCC)(CCCC)CCCC)=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.Cl[Pd]Cl>[Br:10][C:11]1[S:15][C:14]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 15738840(5-Bromothiophen-2-yl)(tributyl)stannane

Product 1

HCID 28205344-(5-Bromothiophen-2-yl)-2-methylsulfanylpyrimidine

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

4-Iodo-2-methylsulfanyl-pyrimidine (2.5 g, 10 mmol), (5-Bromo-thiophen-2-yl)-tributyl-stannane (4.9 g, 11 mmol) and PdCl2 (702 mg, 1 mmol) were heated to 105° C. in toluene (30 ml) for 2 hours. The reaction mixture was poured on water and extracted three times with EtOAc. The combined organic phases were dried over sodium sulfate, filtered, evaporated to dryness and purified via chromatography on silicagel (acetone/hexanes:0/100 to 3/97) to give the title compound as colourless foam. Yield: 1.6 g (55%).

Workup

  1. additionThe reaction mixture was poured on water
  2. extractionextracted three times with EtOAc
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. custompurified via chromatography on silicagel (acetone/hexanes:0/100 to 3/97)

Sources & evidence

ORD record
ord-a96a19d1d0ce424cb13bc0e8cec21ae9
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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