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Lithium aluminum hydride → 4-[1-(1-methyl-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

HRID 1772788
Notes
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Reaction equation

HRID 1772788 reaction equation
[AlH4-].[Li+].[CH3:3][CH:4]([N:13]1[CH:17]=[C:16]([C:18]2[C:19]3[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH:15]=[N:14]1)[C:5](=O)[N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1>C1COCC1>[CH3:3][CH:4]([N:13]1[CH:17]=[C:16]([C:18]2[C:19]3[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH:15]=[N:14]1)[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 670549604-[1-(1-methyl-2-oxo-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 670549204-[1-(1-methyl-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidineYield 27.7%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
3×

Conditions

Temperature
0 °C

Procedure

To a mixture of 1.0 M of lithium tetrahydroaluminate in THF (11.3 mL. 11.3 mmol) in THF (40 mL) was added drop-wise, a solution of 4-[1-(1-methyl-2-oxo-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (2.57 g, 5.64 mmol) in THF (20 mL). The mixture was refluxed for 30 min. The mixture was cooled at 0° C., quenched with 0.44 mL of water, followed by 0.44 mL of 15% NaOH, then 1.32 mL of water. The mixture was stirred at RT for 30 min, filtered through Celite. The filtrate was dried over sodium sulfate, concentrated to dryness under reduced pressure. The resultant residue was purified on silica gel, eluting with 0 to 10% methanol (containing 10% 2M NH3/EtOH) in dichloromethane, to give the desired product (690 mg, 27.7%). LCMS calculated for C22H36N7OSi (M+H)+: m/z=442.3; Found: 442.3.

Workup

  1. additionwas added drop-wise
  2. temperatureThe mixture was refluxed for 30 min
  3. customquenched with 0.44 mL of water
  4. filtrationfiltered through Celite
  5. dry with materialThe filtrate was dried over sodium sulfate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe resultant residue was purified on silica gel
  8. washeluting with 0 to 10% methanol (containing 10% 2M NH3/EtOH) in dichloromethane

Sources & evidence

ORD record
ord-ac366c2d70d341d08f51e808ab8b10f1
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249145B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes