HCID 89630147, compound → HCID 123676383, compound

HRID 882178Notes

Reaction equation

HRID 882178 reaction equation
[CH3:1][C:2]1[N: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)[O:5][CH:6]=1>CO.[OH-].[OH-].[Pd+2]>[CH3:1][C:2]1[N: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)[O:5][CH:6]=1

Participants

4

Reactant 1

HCID 89630147HCID 89630147, compound

Product 1

HCID 123676383HCID 123676383, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-methyl-2-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)oxazole (0.30 g, 0.66 mmol) in methanol (20 mL), was added Pd(OH)2 on carbon (300 mg, 10 wt. %). The flask was purged with hydrogen and was stirred for 4 hours at room temperature under hydrogen atmosphere (1 atm). The reaction was filtered, and concentrated in vacuo to afford crude 3-(5-(4-methyloxazol-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline as a colorless oil. LRMS (ESI) calc'd for C22H28N5O2Si [M+H]+: 422, found 422.

Workup

  1. customThe flask was purged with hydrogen
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19a77e6969574fd69d24035c5c0aee23
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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