Triphenylarsine → HCID 57936158, compound

HRID 1434915Notes

Reaction equation

HRID 1434915 reaction equation
Br[C:2]1[S:6][C:5](/[CH:7]=[CH:8]/[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][S:32][C:33]1[N:38]=[C:37]([Sn](CCCC)(CCCC)CCCC)[CH:36]=[CH:35][N:34]=1>CN1C(=O)CCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:31][S:32][C:33]1[N:38]=[C:37]([C:2]2[S:6][C:5](/[CH:7]=[CH:8]/[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=2)[CH:36]=[CH:35][N:34]=1

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 64271090HCID 64271090, compound

Product 1

HCID 57936158HCID 57936158, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of (E)-4-(5-bromo-thiophen-2-yl)-but-3-en-2-one (1 g, 4.34 mmol), triphenylarsine (319 mg, 1.04 mmol), cuprous iodide (99 mg, 0.52 mmol) and Pd2(dba)3 (119 mg, 0.13 mmol) in 25 ml of NMP was heated to 80° C. To this hot solution 2-methylsulfanyl-4-tributylstannanyl-pyrimidine (1.8 g, 4.34 mmol) dissolved in 10 ml of NMP was added dropwise over a period of 10 minutes. Stirring was continued for 24 hours. The solvent was then removed in vacuo and the residue partitioned between water and EtOAc. The aqueous layer was separated and extracted once more with EtOAc. The combined organic extracts were washed with water and brine, dried over sodium sulfate and evaporated. The crude was purified by chromatography on silicagel (EtOAc/hexane:2/3) to give a yellow solid. Yield: 480 mg (40%).

Workup

  1. additionwas added dropwise over a period of 10 minutes
  2. customThe solvent was then removed in vacuo
  3. customthe residue partitioned between water and EtOAc
  4. customThe aqueous layer was separated
  5. extractionextracted once more with EtOAc
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe crude was purified by chromatography on silicagel (EtOAc/hexane:2/3)
  10. customto give a yellow solid

Sources & evidence

ORD record
ord-8d5868716fff41a29e0954415cc9657c
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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