Imidazole → 5-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-N-phenyl-2-pyrimidinamine

HRID 1890661Notes

Reaction equation

HRID 1890661 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][CH:8]=1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C=O)C.C(OCC)(=O)C>[O:1]([CH2:2][C:3]1[CH:4]=[N:5][C:6]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:7][CH:8]=1)[Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 23156172(2-Anilinopyrimidin-5-yl)methanol

Product 1

HCID 231561235-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-N-phenyl-2-pyrimidinamineYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Hydroxymethyl-2-(phenylamino)pyrimidine (280 mg, 1.39 mmol) obtained in Step 3 was dissolved in DMF (10 mL), and imidazole (190 mg, 2.76 mmol) and tert-butyldimethylsilylchloride (420 mg, 2.79 mmol) were added to the solution, followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10) to obtain 5-(tert-butyldimethylsiloxymethyl)-2-(phenylamino)pyrimidine (423 mg, 82%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-170d9625798e4a61a8a09cc53d4c7ef3
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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