Reaction #2329008

Reaction equation

2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol

tert-butylchlorodimethylsilane

imidazole

tert-butylchlorodimethylsilane

imidazole

→

yellow solid

5-(6-{[tert-butyl(dimethyl)silyl]oxy}-1,3-benzoxazol-2-yl)pyridin-2-amine

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature overnight
2. 2
   OtherThe reaction mixture was then partitioned between EtOAc (100 mL) and water (250 mL)
3. 3
   Extractionthe aqueous layer was extracted twice with EtOAc (100 mL)
4. 4
   WashThe combined organic layers were washed with brine (100 mL)
5. 5
   Dryingdried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated

Procedure

To a solution of 2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol (0.95 mmol) in DMF (25 mL) was added tert-butylchlorodimethylsilane (1.05 mmol) and imidazole (2.38 mmol), the resulting mixture was stirred at room temperature for 3 hours. LCMS showed no conversion. Additional tert-butylchlorodimethylsilane (1.05 mmol) and imidazole (2.38 mmol) was added to the reaction mixture, then stirred at room temperature overnight. The reaction mixture was then partitioned between EtOAc (100 mL) and water (250 mL), and the aqueous layer was extracted twice with EtOAc (100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4), filtered and evaporated to give 1.121 g of a yellow solid. Purified by flash column chromatography (SiO2, Heptane:EtOAc 0→100%), to give the title compound (322.5 mg) as an ivory-white solid. 1H NMR δ ppm 8.67 (d, 1H) 8.01 (dd, 1H) 7.54 (d, 1H) 7.18 (d, 1H) 6.85 (dd, 1H) 6.77 (s, 2H) 6.57 (d, 1H) 0.97 (s, 9H) 0.22 (s, 6H); MS m/z 342 (M+H).

Source