HCID 89630068, compound → HCID 89615616, compound

HRID 882181Notes

Reaction equation

HRID 882181 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]4[O:23][CH:22]=[N:21][CH:20]=4)=[CH:17][N:16]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pt]>[O:23]1[C:19]([C:18]2[C:11]3[C:10]([C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[NH2:1])=[N:15][CH:14]=[N:13][C:12]=3[N:16]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:17]=2)=[CH:20][N:21]=[CH:22]1

Participants

4

Reactant 1

HCID 89630068HCID 89630068, compound

Product 1

HCID 89615616HCID 89615616, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To 5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)oxazole (175 mg, 0.400 mmol) in methanol (5 mL), was added Pt/C (200 mg, 1 wt. % on carbon, Vanadium doped). The atmosphere was then purged with hydrogen gas, and the resulting solution was stirred under hydrogen atmosphere (1 atm) for 3 hours at 25° C. The reaction was filtered and the filtrate concentrated in vacuo to afford crude 3-(5-(oxazol-5-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline as a solid. LRMS (ESI) calc'd for C21H26N5O2Si [M+H]+: 408, found 408.

Workup

  1. customThe atmosphere was then purged with hydrogen gas
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d2d74c7989ea4fa2976d0feca86a283a
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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