Application of 1722-12-9 ,Some common heterocyclic compound, 1722-12-9, molecular formula is C4H3ClN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 5 Synthesis of HK-9, HK-11, HK-13 and HK-15 The following describes the general synthesis of 2-(pyrrolidine-1-yl)pyrimidine (HK-9), 4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine, HK-11, 2-(piperidine-1-yl)pyrimidine (HK-13), 4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (HK-15), 5-benzyloxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 35), 5-benzyloxy-2-(piperidine-1-yl)pyrimidine (Compound 36), 5-benzyloxy-4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 37), and 5-benzyloxy-4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (Compound 38). Referring to the reaction scheme of , to 9.53 mL (116 mmol) pyrrolidine (29) in 400 mL of anhydrous THF was added 2.78 g of sodium hydride (116 mmol) and the mixture was refluxed for 0.5 hr. After cooling to r.t., 12 g (105 mmol) of 2-chloropyrimidine (33) was added dropwise and the mixture was refluxed for 2 days and then cooled in an ice bath. Water (200 mL) was then added to the cooled reaction mixture and the THF was removed in vacuo. The aqueous residue was extracted with CHCl3 and the combined CHCl3 extracts were washed with brine, dried over magnesium sulfate, and filtered. After removal of solvent in vacuo, the residue was purified by silica gel column chromatography using 20:1 hexanes:EtOAc as eluent. The product was then recrystallized from diethyl ether (Et2O) to give a 12.0 g (76%) of HK-9 as a yellow solid, mp 39.0-39.6 C. 1H NMR (CDCl3) delta 8.31 (d, J=4.88 Hz, 2H), 6.45 (t, J=4.88 Hz, 1H), 3.57 (t, J=4.4 Hz, 4H), 2.01-1.98 (m, 4H). Anal. Calcd for C8H11N3; C, 64.40; H, 7.43; N, 28.16. Found: C, 64.42; H, 7.53; N, 27.97.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1722-12-9, its application will become more common.
Reference:
Patent; KADOR, PETER F.; US2014/235858; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia