Methacryloyl chloride → HCID 131732646, compound

HRID 882169Notes

Reaction equation

HRID 882169 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:14]2[C:13]([C:15]3[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=3)[NH2:18])=[N:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:7]=1.CCN(C(C)C)C(C)C.[CH3:39][C:40](=[CH2:44])[C:41](Cl)=[O:42]>C1COCC1>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:14]2[C:13]([C:15]3[CH:16]=[C:17]([NH:18][C:41](=[O:42])[C:40]([CH3:44])=[CH2:39])[CH:19]=[CH:20][CH:21]=3)=[N:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:7]=1

Participants

5

Reactant 3

HCID 13528Methacryloyl chlorideHCID 81531DiisopropylethylamineHCID 89630030HCID 89630030, compound

Product 1

HCID 131732646HCID 131732646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of crude 3-(5-(tetrahydrofuran-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline (410 mg, 1.00 mmol) in THF (10 mL), was added DIPEA (258 mg, 2.00 mmol) followed by dropwise addition of 2-methylprop-2-enoyl chloride (125 mg, 1.20 mmol). The resulting solution was stirred for 4 hours at room temperature prior to being quenched by addition of water. The resulting solution was extracted with ethyl acetate (×3) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 0-100% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford N-(3-(5-(tetrahydrofuran-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as a off-white solid. LRMS (ESI) calc'd for C26H35N4O3Si [M+H]+: 479, found 479.

Workup

  1. customto being quenched by addition of water
  2. extractionThe resulting solution was extracted with ethyl acetate (×3)
  3. washthe combined organic layers were washed with 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 0-100% EtOAc/petroleum ether
  9. customThe product was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa6be39dd1624acc9a131d278937e913
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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