N-bromobutanimide → HCID 89630012, compound

HRID 882165Notes

Reaction equation

HRID 882165 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[CH:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1C(=O)N([Br:34])C(=O)C1>CC#N>[Br:34][C:18]1[C:11]2[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:15][CH:14]=[N:13][C:12]=2[N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 123358842HCID 123358842, compound

Product 1

HCID 89630012HCID 89630012, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (4.40 g, 11.9 mmol) in CH3CN (25 mL), was added NBS (3.60 g, 20.2 mmol). The resulting solution was stirred for 30 minutes at 80° C. before being concentrated in vacuo. The reaction was diluted with ethyl acetate (200 mL), washed with water (×3), and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 2-6% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 5-bromo-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine as a yellow oil. LRMS (ESI) calc'd for C18H22N4O3SiBr [M+H]+: 449, found 449.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. additionThe reaction was diluted with ethyl acetate (200 mL)
  3. washwashed with water (×3)
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe reaction was then purified by chromatography
  8. washeluting with 2-6% EtOAc/petroleum ether
  9. customThe product was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4bffe3758d64022a2fe39c4aa67f785
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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