Reference of 56686-16-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 56686-16-9 as follows.
t-BuLi (Aldrich; 1.7 M soln in pentane, 1.1 mL) was added to a mixture of 8 (Aldrich; 200 mg, 0.9 mmol) and dry THF (2 mL) at -78 C under argon. The mixture was left at -78 C for 30 min and then compound 3 (190 mg, 0.8 mmol) was added. The mixture was allowed to warm to room temperature. The reaction was followed by TLC (CHCl3/acetone, 85/15, v/v) at 30 min intervals. After stirring for 3 h at room temperature, when 3 was no longer detected by TLC, Et2O (20 mL) was added. The mixture was washed with H2O (5 mL) and evaporated to dryness. The residue was dissolved in 1,4-dioxane (6 mL) and CH2Cl2 (2 mL). Cu(OAc)2 (40 mg), NH3 (aq) (0.3 mL) and H2O (1 mL) were added. The mixture was stirred at room temperature for 1 d. The organic layer was separated, washed with H2O (10 mL), dried (MgSO4) and concentrated to dryness. Column chromatography of the residue (CHCl3/acetone, 85/15, v/v) gave 9 (70 mg, 39%), 10 (89 mg, 71%), and 11 (50 mg, 17%). 9: A white solid (mp >180 C, dec). deltaH (CDCl3, 200 MHz) 1.43-1.56 (16H, m), 1.90 (4H, m), 2.35 (4H, m), 3.29 (4H, m), 3.56 and 4.34 (8H, AB quartet, 2JAB 11.4 Hz); deltaC (CDCl3, 50 MHz) 22.34, 22.58, 25.42, 26.16, 27.48, 28.49, 36.98, 64.28, 66.43, 72.57, 98.80, 136.38; numax (KBr) 2936, 2860, 1496, 1448, 1380, 1240, 1156, 1044, 920; HRMS (EI, 70 eV) m/z calcd for C24H36O6N2 (M+) 448.2573, found 448.2557. 11: A white solid (mp 151-152 C). deltaH (CDCl3, 200 MHz) 1.34-1.84 (8H, m), 2.1 (2H, m), 2.39 (2H, m), 3.12 (2H, m), 3.63 and 4.57 (4H, AB quartet, 2JAB 11.4), 4.00 (3H, s), 4.02 (3H, s), 10.09 (1H, s); deltaC (CDCl3, 50 MHz) 22.39, 22.67, 25.49, 27.42, 28.21, 28.84, 37.29, 54.21, 55.19, 64.36, 72.23, 98.77, 105.98, 136.72, 159.26, 165.04, 167.74; numax (KBr) 2948, 2936, 1716, 1688, 1556, 1536, 1480, 1464, 1356, 1252, 1244, 1108; HRMS (EI, 70 eV) m/z calcd for C18H25O5N3 (M+) 363.1794, found 363.1812. The NMR spectra of 10 were consistent with those described: H. Pelissier, J. Rodriguez and K.P.C. Volhardt, Chem. Eur. J. 5 (1999), p. 3549. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (27)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56686-16-9, its application will become more common.
Reference:
Article; Koszytkowska-Stawi?ska, Mariola; Mironiuk-Puchalska, Ewa; Sas, Wojciech; Tetrahedron Letters; vol. 52; 16; (2011); p. 1866 – 1870;,
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