(S)-benzyl 3-(ethyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate → (S)-N-ethyl-N-(piperidin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 919582Notes

Reaction equation

HRID 919582 reaction equation
[CH2:1]([N:3]([C:20]1[C:21]2[CH:28]=[CH:27][N:26]([S:29]([C:32]3[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:22]=2[N:23]=[CH:24][N:25]=1)[C@H:4]1[CH2:9][CH2:8][CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[CH2:5]1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([N:3]([C@H:4]1[CH2:9][CH2:8][CH2:7][NH:6][CH2:5]1)[C:20]1[C:21]2[CH:28]=[CH:27][N:26]([S:29]([C:32]3[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=3)(=[O:30])=[O:31])[C:22]=2[N:23]=[CH:24][N:25]=1)[CH3:2]

Participants

4

Reactant 1

HCID 86706456(S)-benzyl 3-(ethyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Product 1

HCID 118906729(S)-N-ethyl-N-(piperidin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 61.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-benzyl 3-(ethyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (130 mg, 0.243 mmol), 10% Pd/C (130 mg) in ethanol (4 mL) was placed under an atmosphere of hydrogen (1 atm) for 1 h. The reaction mixture was filtered through a celite pad and the filtrate was concentrated in vacuo to yield the title intermediate (60 mg, 61%). LC-MS: m/z [M+1]=400.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-958e54f5e6e74b5087f0af092c294d70
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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