HCID 123358842, compound → HCID 89630145, compound

HRID 882158Notes

Reaction equation

HRID 882158 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-])=O>CO.[Pd]>[CH3:24][Si:23]([CH3:26])([CH3:25])[CH2:22][CH2:21][O:20][CH2:19][N:16]1[C:12]2[N:13]=[CH:14][N:15]=[C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[NH2:1])[C:11]=2[CH:18]=[CH:17]1

Participants

4

Reactant 1

HCID 123358842HCID 123358842, compound

Product 1

HCID 89630145HCID 89630145, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (12.0 g, 32.4 mmol) in methanol (200 mL), was added Pd/C (2.00 g, 10 wt. %). The reaction was then purged with hydrogen gas and stirred overnight at room temperature under hydrogen atmosphere (1 atm) before being filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 50% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 3-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline as a yellow oil. LRMS (ESI) calc'd for C18H25N4OSi [M+H]+: 341, found 341.

Workup

  1. customThe reaction was then purged with hydrogen gas
  2. filtrationbefore being filtered
  3. concentrationconcentrated in vacuo
  4. customThe reaction was then purified by chromatography
  5. washeluting with 50% EtOAc/petroleum ether
  6. customThe product was collected
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d9ec5c3938a44a08a4c424c7d774e48
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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