(S)-3-Isopropyl-2,5-piperazinedione → (S)-2-Isopropylpiperazine

HRID 1892128Notes

Reaction equation

HRID 1892128 reaction equation
[CH:1]([C@@H:4]1[NH:9][C:8](=O)[CH2:7][NH:6][C:5]1=O)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:1]([C@H:4]1[CH2:5][NH:6][CH2:7][CH2:8][NH:9]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 736942(S)-3-Isopropyl-2,5-piperazinedioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 15023839(S)-2-Isopropylpiperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-3-isopropylpiperazine-2,5-dione (100 mg, 0.6 mmol) in anhydrous THF was added lithium aluminum hydride 1M in THF (1.2 ml, 1.2 mmol). The reaction refluxed for 1 hr, cooled to room temperature, quenched with H2O, filtered, then concentrated under vacuum to yield (S)-2-isopropylpiperazine. This material was combined with 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (85.5 mg, 0.5 mmol) in triethylamine (1 ml) and isopropanol (2 ml). The reaction was heated in a microwave at 180° C. for 30 min, concentrated under vacuum, dissolved in EtOAc, washed with H2O, and concentrated under vacuum to afford (S)-4-(3-isopropylpiperazin-1-yl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine, carried on without further purification.

Workup

  1. temperatureThe reaction refluxed for 1 hr
  2. customquenched with H2O
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f4cc17c868c249b1996119a431102d1f
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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