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

HRID 524418Notes

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]

Participants

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

customconsumption of starting material
temperatureThe reaction mixture was cooled to room temperature
additionpoured into water
extractionextracted with ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure
customto get the crude product which
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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