| Identification | Back Directory | [Name]
tert-butyl 2-methoxypyridin-3-ylcarbamate | [CAS]
161117-83-5 | [Synonyms]
tert-butyl 2-methoxypyridin-3-ylcarbamate
3-(N-tert-butoxycarbonylaMino)-2-Methoxypyridine
CarbaMic acid, (2-Methoxy-3-pyridinyl)-, 1,1-diMethylethyl ester
Carbamic acid, N-(2-methoxy-3-pyridinyl)-, 1,1-dimethylethyl ester | [Molecular Formula]
C11H16N2O3 | [MDL Number]
MFCD11100821 | [MOL File]
161117-83-5.mol | [Molecular Weight]
224.26 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 |
|
|