Sodium borohydride → 3-methyl-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

HRID 1692952Notes

Reaction equation

HRID 1692952 reaction equation
Br[CH2:2][CH:3]1[CH2:6][C:5]([CH2:29][C:30]#[N:31])([N:7]2[CH:11]=[C:10]([C:12]3[C:13]4[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:14]=4[N:15]=[CH:16][N:17]=3)[CH:9]=[N:8]2)[CH2:4]1.[BH4-].[Na+]>CN(C=O)C>[CH3:2][CH:3]1[CH2:4][C:5]([CH2:29][C:30]#[N:31])([N:7]2[CH:11]=[C:10]([C:12]3[C:13]4[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[C:14]=4[N:15]=[CH:16][N:17]=3)[CH:9]=[N:8]2)[CH2:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 670172173-(bromomethyl)-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

Product 1

HCID 670172343-methyl-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Bromomethyl)-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile (0.65 g, 0.0013 mol) was reacted with sodium tetrahydroborate (0.096 g, 0.0026 mol) in DMF (5.2 mL) (˜0.5 M) at rt under nitrogen for 3h. The reaction was quenched with water and extracted with dichloromethane. The organic layers were washed with water, brine, dried over MgSO4 and concentrated to give a yellow oil, the desired product as cis- and trans-isomer mixtures. LCMS calculated for C22H31N6OSi(M+H)+: 423.2; Found: 423.4.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-5be58b6d944c4525bd875568998e276e
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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