Tetramethyltin → HCID 71059779, compound

HRID 241456Notes

Reaction equation

HRID 241456 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[N:16][C:11]3=[N:10][C:9]=2[CH3:17])=[CH:4][CH:3]=1.[CH3:18][Sn](C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH3:17][C:9]1[N:10]=[C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]2[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:18])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 71059821HCID 71059821, compound

Product 1

HCID 71059779HCID 71059779, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Add 3-(4-bromophenyl)-2-methyl-imidazo[1,2-a]pyrimidine (1.00 g, 3.470 mmol) and DMF (17 mL) to a 50 mL screw-cap vial (fitted with stir bar). Degas the solution with nitrogen for 3 min. Add tetramethylstannane (1.91 mL, 13.88 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.36 g, 520.57 μmol) to the vial, and close the vial. Heat the mixture in an oil bath to 130° C. for 2 hours. Cool the reaction to room temperature, and quench with an excess of water. Extract the mixture with EtOAc. Wash the combined organic extracts with brine. Dry the organic extracts over potassium carbonate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the crude mixture by silica gel chromatography with a gradient of 50-100% hexane/EtOAc to give the title compound as a white solid (0.50 g, 64% yield). LCMS (m/z) 224.2 (M+1). 1H NMR (399.83 MHz, d6-DMSO) δ 8.81-8.79 (m, 1H), 8.51-8.49 (m, 1H), 7.73 (d, J=7.9 Hz, 2H), 7.31 (d, J=7.9 Hz, 2H), 7.09-7.06 (m, 1H), 2.64 (s, 3H), 2.36 (s, 3H).

Workup

  1. customscrew-cap vial
  2. custom(fitted with stir bar)
  3. customDegas the solution with nitrogen for 3 min
  4. temperatureCool
  5. customthe reaction to room temperature
  6. customquench with an excess of water
  7. extractionExtract the mixture with EtOAc
  8. washWash the combined organic extracts with brine
  9. dry with materialDry the organic extracts over potassium carbonate
  10. filtrationfilter
  11. customcollect the filtrate
  12. concentrationand concentrate the filtrate under reduced pressure
  13. customPurify the crude mixture by silica gel chromatography with a gradient of 50-100% hexane/EtOAc

Sources & evidence

ORD record
ord-5f9bee927ca241c9ba4e258923b257a5
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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