tert-butyl 2-methoxypyridin-3-ylcarbamate Chemical Properties

Boiling point:

276.0±25.0 °C(Predicted)

Density 

1.146±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

12.31±0.70(Predicted)

tert-butyl 2-methoxypyridin-3-ylcarbamate Usage And Synthesis

Synthesis

To a 2000 mL three-necked flask was added 2-methoxy-3-aminopyridine (100 g, 0.8 mol, 1.0 equiv), di-tert-butyl dicarbonate (194 g, 0.89 mol, 1.1 equiv) and 1,4-dioxane (1140 mL, 11.4 vol). The reaction mixture was heated to reflux and kept for 4 h. The progress of the reaction was monitored by thin layer chromatography (TLC) (Expander: ethyl acetate/petroleum ether = 1:4, Rf of raw material = 0.3, Rf of product = 0.55) until the raw material disappeared completely. After completion of the reaction, the reaction mixture was concentrated to afford tert-butyl 2-methoxypyridine-3-carbamate as a dark colored oil (181 g, 100% yield).1H NMR (400 MHz, DMSO-d6): δ 1.47 (s, 9H), 3.91 (s, 3H), 6.95 (m, 1H), 7.84 (m, 1H), 7.98 (d, J =8.1 Hz, 1H), 8.17 (br s, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6041 - 6045
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5292 - 5296
[3] Patent: US6339097, 2002, B1. Location in patent: Page column 13
[4] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 18, p. 2221 - 2226
[5] Tetrahedron Letters, 1994, vol. 35, # 48, p. 9003 - 9006

tert-butyl 2-methoxypyridin-3-ylcarbamate(161117-83-5)Related Product Information

• 2-METHOXY-3-(BOC-AMINO)-4-TRIFLUORO-ACETYLPYRIDINE
• tert-butyl 2-methoxypyridin-3-ylcarbamate