2,3-Dihydrofuran → HCID 89630016, compound

HRID 882167Notes

Reaction equation

HRID 882167 reaction equation
Br[C:2]1[C:10]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1.CC([O-])=O.[Na+].[O:33]1[CH:37]=[CH:36][CH2:35][CH2:34]1>CN(C)C=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2]>[O:33]1[CH2:37][CH:36]=[CH:35][CH:34]1[C:2]1[C:10]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1

Participants

7

Reactant 3

HCID 709342,3-DihydrofuranHCID 517045Sodium AcetateHCID 89630012HCID 89630012, compound

Product 1

HCID 89630016HCID 89630016, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a degassed solution of 5-bromo-4-(3-nitrophenyl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine (1.30 g, 2.89 mmol) in N,N-dimethylformamide (40 mL), was added Pd(OAc)2 (650 mg, 2.90 mmol), Bu4NCl (1.00 g, 3.60 mmol), NaOAc (714 g, 8.71 mol) and 2,3-dihydrofuran (2.00 g, 28.5 mmol). The reaction was stirred for 2 hours at 50° C. and then quenched by the addition of water. The resulting solution was extracted with ethyl acetate (×3), and the organic layers were combined, washed with water, brine, then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-50% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 5-(2,5-dihydrofuran-2-yl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine as a yellow oil. LRMS (ESI) calc'd for C22H27N4O4Si [M+H]+: 439, found 439.

Workup

  1. customquenched by the addition of water
  2. extractionThe resulting solution was extracted with ethyl acetate (×3)
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe reaction was purified by chromatography
  8. washeluting with 1-50% EtOAc/petroleum ether
  9. customThe product was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7851d51f0a84f0fa415fe9e28660960
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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