N-bromobutanimide → HCID 89629894, compound

HRID 882160Notes

Reaction equation

HRID 882160 reaction equation
[CH3:1][Si:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[C:18]([NH:22][C:23](=[O:27])[C:24]([CH3:26])=[CH2:25])[CH:19]=[CH:20][CH:21]=3)[C:10]=2[CH:9]=[CH:8]1.C1C(=O)N([Br:37])C(=O)C1>CC#N>[Br:37][C:9]1[C:10]2[C:15]([C:16]3[CH:17]=[C:18]([NH:22][C:23](=[O:27])[C:24]([CH3:26])=[CH2:25])[CH:19]=[CH:20][CH:21]=3)=[N:14][CH:13]=[N:12][C:11]=2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:28])[CH3:29])[CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 89630019HCID 89630019, compound

Product 1

HCID 89629894HCID 89629894, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(3-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide (5.20 g, 12.7 mmol) in CH3CN (80 mL), was added NBS (2.40 g, 13.5 mmol) in several portions at 80° C. The resulting solution was stirred for 2 hours at 80° C. before being concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 0-33% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford N-(3-(5-bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as a yellow solid. LRMS (ESI) calc'd for C22H28N4O2SiBr [M+H]+: 487, found 487.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe reaction was then purified by chromatography
  3. washeluting with 0-33% EtOAc/petroleum ether
  4. customThe product was collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4056d086c59f4a22b02b30800e3dfc3e
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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