(R)-3-{3-[5-(2-Trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid benzyl ester → (R)-pyrrolidin-3-yl-{3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-amine

HRID 1916095Notes

Reaction equation

HRID 1916095 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][C@@H:13]([NH:16][C:17]2[C:22]([C:23]3[N:24]=[C:25]4[CH:31]=[CH:30][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:26]4=[N:27][CH:28]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:12]1)=O)C1C=CC=CC=1>CCO>[NH:11]1[CH2:15][CH2:14][C@@H:13]([NH:16][C:17]2[C:22]([C:23]3[N:24]=[C:25]4[CH:31]=[CH:30][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:26]4=[N:27][CH:28]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:12]1

Participants

3

Reactant 1

HCID 58177277(R)-3-{3-[5-(2-Trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 69812726(R)-pyrrolidin-3-yl-{3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-amineYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-{3-[5-(2-Trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid benzyl ester (0.535 g, 0.98 mmol) was dissolved in 20 ml of EtOH and the flask was flushed with argon. 20% Pd(OH)2/C (0.105 g) was added and the system was flushed with argon again and at last was flushed with hydrogen. A hydrogen balloon was placed on the flask, with a needle, so that the gas bubbled directly into the solution at atmospheric pressure and the reaction was left for 2 h. The catalyst was removed by filtration and the solution was concentrated to dryness, giving 0.330 g (81%) of (R)-pyrrolidin-3-yl-{3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-amine which was used as is in the following steps.

Workup

  1. customthe flask was flushed with argon
  2. addition20% Pd(OH)2/C (0.105 g) was added
  3. customthe system was flushed with argon again
  4. customat last was flushed with hydrogen
  5. custombubbled directly into the solution at atmospheric pressure
  6. customThe catalyst was removed by filtration
  7. concentrationthe solution was concentrated to dryness

Sources & evidence

ORD record
ord-87a01b3efbcc4b839d5450c2760922c7
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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