Methacryloyl chloride → HCID 89630019, compound

HRID 882159Notes

Reaction equation

HRID 882159 reaction equation
[CH3:1][Si:2]([CH3:24])([CH3:23])[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]([CH:20]=[CH:21][CH:22]=3)[NH2:19])[C:10]=2[CH:9]=[CH:8]1.CCN(C(C)C)C(C)C.[CH3:34][C:35](=[CH2:39])[C:36](Cl)=[O:37]>ClCCl>[CH3:1][Si:2]([CH3:24])([CH3:23])[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:19][C:36](=[O:37])[C:35]([CH3:39])=[CH2:34])[CH:20]=[CH:21][CH:22]=3)[C:10]=2[CH:9]=[CH:8]1

Participants

5

Reactant 3

HCID 13528Methacryloyl chlorideHCID 81531DiisopropylethylamineHCID 89630145HCID 89630145, compound

Product 1

HCID 89630019HCID 89630019, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of 3-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline (10.0 g, 29.4 mmol) in dichloromethane (200 mL), was added DIPEA (12.0 g, 92.9 mmol) followed by dropwise addition of a solution of 2-methylprop-2-enoyl chloride (4.60 g, 44.0 mmol) in dichloromethane (50 mL) at −5 to 0° C. The reaction was stirred overnight at room temperature, quenched by addition of water (150 mL), and extracted with dichloromethane (×3). The organic layers were combined, washed with water and HCl solution (0.5 M in water), dried over anhydrous sodium sulfate, filtered and 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-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as a yellow oil. LRMS (ESI) calc'd for C22H29N4O2Si [M+H]+: 409, found 409.

Workup

  1. customquenched by addition of water (150 mL)
  2. extractionextracted with dichloromethane (×3)
  3. washwashed with water and HCl solution (0.5 M in water)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe reaction was then purified by chromatography
  8. washeluting with 0-33% EtOAc/petroleum ether
  9. customThe product was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1aba4a4a8beb44efa958a4ead6155717
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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