Imidazole → 3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

HRID 452208Notes

Reaction equation

HRID 452208 reaction equation
N1C=CN=C1.[C:6]([Si:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)Cl)([CH3:9])([CH3:8])[CH3:7].[OH:24][CH2:25][C:26]1[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=1.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Si:10]([O:24][CH2:25][C:26]1[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 106304823-(Hydroxymethyl)pyridin-2(1H)-one

Product 1

HCID 594101563-({[tert-Butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

At RT, 0.65 g (9.59 mmol) of imidazole, 2.42 g (8.79 mmol) of t-butyldiphenylchlorosilane and 0.10 g (0.80 mmol) of DMAP are added to 1.00 g (7.99 mmol) of the compound from Example 2A in 19 ml of DMF, and the mixture is stirred for 18 h. 180 ml of water are then added, and the mixture is kept at 0° C. for 3 h. After filtration, the residue obtained is purified by chromatography on silica gel (ethyl acetate/ethyldimethylamine 1000:1). This gives 801 mg (27% of theory) of the desired compound.

Workup

  1. waitthe mixture is kept at 0° C. for 3 h
  2. filtrationAfter filtration
  3. customthe residue obtained
  4. customis purified by chromatography on silica gel (ethyl acetate/ethyldimethylamine 1000:1)

Sources & evidence

ORD record
ord-76a7f4c7be344828b290e2efcc22189e
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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