2-(Tributylstannyl)furan → HCID 10172251, compound

HRID 457696Notes

Reaction equation

HRID 457696 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[C:15](Br)[N:16]3[CH2:19][CH3:20])=[C:12]([NH2:22])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn]([C:36]1[O:37][CH:38]=[CH:39][CH:40]=1)(CCCC)CCCC)CCC>O1CCCC1.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>[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[C:15]([C:36]4[O:37][CH:38]=[CH:39][CH:40]=4)[N:16]3[CH2:19][CH3:20])=[C:12]([NH2:22])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 10309103HCID 10309103, compound

Product 1

HCID 10172251HCID 10172251, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(2-phenylethylamino)-8-bromo-9-ethyl-9H-purin-6-ylamine (0.28 mmol), tributylstannyl furan (440 μL, 1.4 mmol), and bis(triphenylphosphine)palladium dichloride (12 mg, 0.017 mmol) was dissolved in dry tetrahydrofuran (10 mL), and heated at 60° C. for 3 hours. The solvent was removed in vacuo, and the residue was partitioned between water and chloroform. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in CHCl3/MeOH and extracted with chloroform. The organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on a silica gel column eluting with ethyl acetate/cyclohexane/methanol (60/36/4) to give 2-(2-phenylethylamino)-8-(furan-2-yl)-9-ethyl-9H-purin-6-ylamine as a chromatographically pure solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and chloroform
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in CHCl3/MeOH
  7. extractionextracted with chloroform
  8. dry with materialThe organic layers were dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed on a silica gel column
  11. washeluting with ethyl acetate/cyclohexane/methanol (60/36/4)

Sources & evidence

ORD record
ord-d004288931d3438b8952a8a2615d315f
Source dataset
uspto-grants-2007_03
Patent number
US07189730B2

Reaction notes

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