tert-Butanol → HCID 21106657, compound

A solution of 2-chloro-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridine (from Example 4; 100 mg, 0.39 mmol), 2-(methylamino)ethanol (47 μl, 0.58 mmol) and 1.0 M potassium tert-butoxide in tert-butanol (0.8 mL, 0.80 mmol) in 4 mL of toluene was heated at 100° C. for 1 day. The organic phase was washed with 3×2 mL of 1.0 M NaOH and 1 mL of brine. The organic phase was shaken with 4 mL of 2.0 M acetic acid for 2 days. The aqueous phase was washed with 3×3 mL of ethyl acetate, made basic by addition of potassium hydroxide, saturated with sodium chloride and extracted with 3×2 mL of chloroform. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give 12 mg (0.056 mmol, 14%) of the title compound as a colorless oil. LC-UV purity 90%. MS m/z 213 (M+1)+, calc. 213 (M+1)+.

1. washThe organic phase was washed with 3×2 mL of 1.0 M NaOH and 1 mL of brine
2. washThe aqueous phase was washed with 3×3 mL of ethyl acetate
3. additionmade basic by addition of potassium hydroxide, saturated with sodium chloride
4. extractionextracted with 3×2 mL of chloroform
5. dry with materialThe organic phase was dried (MgSO4)
6. concentrationconcentrated under reduced pressure

ORD record

ord-a39a55472a60476e9b739ace19a72833

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07226925B2