Diisobutylaluminumhydride → 3-Methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butan-1-ol

HRID 44927Notes

Reaction equation

HRID 44927 reaction equation
[CH3:1][C:2]([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)([CH3:9])[CH2:3][C:4](OCC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.C(Cl)Cl>[CH3:9][C:2]([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:29])[CH3:30])[C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)([CH3:1])[CH2:3][CH2:4][OH:5]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66597630Ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]butanoate

Product 1

HCID 574776113-Methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butan-1-olYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]butanoate (15.4 g, 0.0347 mol) in THF (151 mL) at −78° C. was added 1.00 M diisobutylaluminum hydride in DCM (84.5 mL) dropwise. The reaction was stirred for 2 hours with slow warming to −10° C. The mixture was quenched with water, then was treated with potassium sodium tartrate tetrahydrate and water. The mixture was stirred for 1 hour, then was extracted with ethyl acetate. The extracts were washed with water and brine, then dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (13.8 g, 99%).

Workup

  1. customThe mixture was quenched with water
  2. additionwas treated with potassium sodium tartrate tetrahydrate and water
  3. stirringThe mixture was stirred for 1 hour
  4. extractionwas extracted with ethyl acetate
  5. washThe extracts were washed with water and brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b34315ffdf4c42c3bc3eee47fe4b7496
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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