HCID 89630146, compound → HCID 89630034, compound

HRID 882173Notes

Reaction equation

HRID 882173 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[C:15]3[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:8]=2)=[N:5][N:6]=1>CO.[Pd]>[CH3:1][C:2]1[O:3][C:4]([C:7]2[C:15]3[C:14]([C:16]4[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=4)[NH2:22])=[N:13][CH:12]=[N:11][C:10]=3[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:8]=2)=[N:5][N:6]=1

Participants

4

Reactant 1

HCID 89630146HCID 89630146, compound

Product 1

HCID 89630034HCID 89630034, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-5-[4-(3-nitrophenyl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-1,3,4-oxadiazole (0.40 g, 0.88 mmol) in methanol (10 mL), was added Pd on carbon (200 mg, 10 wt. %). The atmosphere was purged with hydrogen and the reaction was stirred for 12 hours at room temperature under a hydrogen atmosphere (1 atm). The solution was filtered and the filtrate was concentrated in vacuo to afford crude 3-(5-(5-methyl-1,3,4-oxadiazol-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline as a black solid. LRMS (ESI) calc'd for C21H27N6O2Si [M+H]+: 423, found 423.

Workup

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

Sources & evidence

ORD record
ord-1aad86919c474e379be2c781793f6d60
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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