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Imidazole → 5-[3-[[Tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]thiazol-2-amine

HRID 524418
Notes
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Reaction equation

HRID 524418 reaction equation
[NH2:1][C:2]1[S:3][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[CH:5][N:6]=1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[Si:20]([O:15][CH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][C:4]1[S:3][C:2]([NH2:1])=[N:6][CH:5]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86669548[3-(2-Aminothiazol-5-yl)oxyphenyl]methanol

Product 1

HCID 866695505-[3-[[Tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]thiazol-2-amineYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

[3-(2-aminothiazol-5-yl)oxyphenyl]methanol (1.70 g, 7.575 mmol), tert-butyldimethylchlorosilane (1.38 g, 9.189 mmol), and imidazole (0.625 g, 9.189 mmol) was taken in 20 mL of dry DMF and heated at 60° C. for overnight. TLC showed consumption of starting material. The reaction mixture was cooled to room temperature and poured into water and extracted with ethyl acetate. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get the crude product which was purified by column chromatography using 5-30% ethyl acetate in hexanes to get pure title compound (0.998 g).

Workup

  1. customconsumption of starting material
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionpoured into water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customto get the crude product which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d5a50fadec024ef3be2992115347627b
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09340506B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes