Sodium borohydride → HCID 67279657, compound

HRID 1692954Notes

Reaction equation

HRID 1692954 reaction equation
CS(O[CH2:6][C:7]1([CH2:36]OS(C)(=O)=O)[CH2:10][C:9]([CH2:33][C:34]#[N:35])([N:11]2[CH:15]=[C:14]([C:16]3[C:17]4[CH:24]=[CH:23][N:22]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]=4[N:19]=[CH:20][N:21]=3)[CH:13]=[N:12]2)[CH2:8]1)(=O)=O.[BH4-].[Na+]>CN(C=O)C>[CH3:6][C:7]1([CH3:36])[CH2:8][C:9]([CH2:33][C:34]#[N:35])([N:11]2[CH:15]=[C:14]([C:16]3[C:17]4[CH:24]=[CH:23][N:22]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[C:18]=4[N:19]=[CH:20][N:21]=3)[CH:13]=[N:12]2)[CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86634350HCID 86634350, compound

Product 1

HCID 67279657HCID 67279657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Cyanomethyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutane-1,1-diylbis(methylene) dimethanesulfonate (0.06 g, 0.0001 mol) was reacted with sodium tetrahydroborate (0.02 g, 0.0004 mol) in DMF (0.8 mL) (˜0.5 M) at 65° C. under nitrogen for 2 h. The reaction was quenched with water, and extracted with dichloromethane. The organic layers were washed with water, dried over MgSO4, concentrated. The residue was purified with Combiflash (silica gel, 0-60% EtOAc/Hex) to give the desired product. LCMS calculated for C23H33N6OSi(M+H)+: 437.2; Found: 437.4.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with Combiflash (silica gel, 0-60% EtOAc/Hex)

Sources & evidence

ORD record
ord-5567ce525aed450395264eac90818505
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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