N-(1-Benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine → N-Methyl-N-[(3S,4S)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2122045Notes

Reaction equation

HRID 2122045 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH:10]([N:15]([CH3:25])[C:16]2[C:17]3[CH:24]=[CH:23][NH:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:25][N:15]([CH:10]1[CH:11]([CH3:14])[CH2:12][CH2:13][NH:8][CH2:9]1)[C:16]1[C:17]2[CH:24]=[CH:23][NH:22][C:18]=2[N:19]=[CH:20][N:21]=1

Participants

4

Reactant 1

HCID 12084829N-(1-Benzyl-4-methylpiperidin-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 12084830N-Methyl-N-[(3S,4S)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To the product from Method G (0.7 grams, 2.19 mmol) dissolved in 15 mL of ethanol was added 0.5 grams of 20% palladium hydroxide on carbon (50% water) (Aldrich) and the resulting mixture agitated (Parr-Shaker) under an atmosphere of hydrogen (50 psi) at room temperature for 2 days. The Celite filtered reaction mixture was concentrated to dryness in vacuo and the residue purified by flash chromatography (silica; 5% methanol in dichoromethane) affording 0.48 grams (90%) of the title compound. LRMS: 246.1 (M+1).

Workup

  1. filtrationThe Celite filtered
  2. customreaction mixture
  3. concentrationwas concentrated to dryness in vacuo
  4. customthe residue purified by flash chromatography (silica; 5% methanol in dichoromethane)

Sources & evidence

ORD record
ord-835f2818c48f4da1988dd42305784ad2
Source dataset
uspto-grants-2004_02
Patent number
US06696567B2

Reaction notes

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