Imidazole → HCID 59678615, compound

HRID 1516093Notes

Reaction equation

HRID 1516093 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH2:12][OH:13])=[C:8]([Cl:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C=O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH2:12][O:13][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[C:8]([Cl:14])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 59678687HCID 59678687, compound

Product 1

HCID 59678615HCID 59678615, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-tert-butyl-4-hydroxymethyl-5-chloro 3(2H)-pyridazinone (1 g, 4.62 mmol) is dissolved in DMF in a 25 ml round bottom flask and to this were added imidazole (0.377 g, 5.0 mmol) and tert-butyldimethylsilyl chloride (0.762 g, 3.09 mmol). The mixture is stirred for 10 hours after which it is extracted in dichloromethane and the organic layer washed with water and dried. Purification by flash chromatography (silica gel; ethyl acetate/hexanes) affords the above mentioned product.

Workup

  1. extractionis extracted in dichloromethane
  2. washthe organic layer washed with water
  3. customdried
  4. customPurification by flash chromatography (silica gel; ethyl acetate/hexanes)
  5. customaffords the

Sources & evidence

ORD record
ord-d6133135e3c24ca3920f1c3b693ce553
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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