Butyl iodide → HCID 15658018, compound

Temperature

0 °C

To 2-amino-3-benzyloxypyridine (2.50 g, 12.5 mmol) dissolved in tetrahydrofuran (10 mL) and cooled to 0° C. was slowly added a solution of 1N lithium hexamethyldisilazide in tetrahydrofuran (12.5 mL, 12.5 mmol). The ice bath was removed and the solution stirred for 30 minutes. The bath was replaced and n-butyl iodide (2.30 g, 1.4 mL, 12.5 mmol) was added to the solution. After the addition was complete, the bath was removed and the solution stirred at ambient temperature overnight. The reaction mixture was evaporated in vacuo and the residue dissolved in ethyl acetate (25 mL). The solution was washed with water (25 mL) and brine (25 mL), dried and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with 10% ethyl acetate in hexane afforded the desired product as an offwhite solid (2.75 g, 86% yield). 1H NMR (CDCl3, 300 MHz) δ 0.95 (t, J=7 Hz, 3 H), 1.42 (sextet, J=7 Hz, 2H), 1.60 (m, 2H), 3.44 (dt, J=7 Hz, 1 Hz, 2H), 4.92 (bt, 1H), 5.06 (s, 2H), 6.45 (dd, J=8 Hz, 6 Hz 1H), 6.86 (dd, J=8 Hz, 1 Hz, 1H), 7.37 (m, 5H), 7.73 (dd, J=6 Hz, 1 Hz, 1H). MS (DCl/NH3) m/e 257 (M+H)+.

1. customThe ice bath was removed
2. additionAfter the addition
3. customthe bath was removed
4. stirringthe solution stirred at ambient temperature overnight
5. customThe reaction mixture was evaporated in vacuo
6. dissolutionthe residue dissolved in ethyl acetate (25 mL)
7. washThe solution was washed with water (25 mL) and brine (25 mL)
8. customdried
9. concentrationconcentrated in vacuo
10. customPurification by flash chromatography on silica gel eluting with 10% ethyl acetate in hexane

ORD record

ord-9a56b424f3be4284b6d4d5f659dd0057

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250548