Imidazole → HCID 178455181, compound

HRID 1599286Notes

Reaction equation

HRID 1599286 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[N:6]=[CH:7][N:8]=[CH:9][C:10]=2[N:11]=1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1.CN(C)C=O>O>[Si:12]([O:1][CH2:2][C:3]1[NH:4][C:5]2[N:6]=[CH:7][N:8]=[CH:9][C:10]=2[N:11]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178519944HCID 178519944, compound

Product 1

HCID 178455181HCID 178455181, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.81 g of 2-hydroxymethyl-3H-imidazo[5,4-d]pyrimidine (prepared as described in Preparation 48), 2.71 g of t-butyldimethylsilyl chloride, 2.45 g of imidazole and 100 ml of dimethylformamide was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was freed from dimethylformamide by distillation under reduced pressure. The residue thus obtained was diluted with water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 1.89 g of the title compound, melting at 104°-107° C.

Workup

  1. distillationAt the end of this time, the reaction mixture was freed from dimethylformamide by distillation under reduced pressure
  2. customThe residue thus obtained
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-c42b593682f345cab9816bbdf795fced
Source dataset
uspto-grants-1998_04
Patent number
US05739345

Reaction notes

Loading…