Electric Literature of 3435-25-4 ,Some common heterocyclic compound, 3435-25-4, molecular formula is C5H5ClN2, 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.
To a stirred solution of 4-chloro-6-methylpyrimidine (1 g, 7.77 mmol) in 1, 4- dioxane (30 mL) under argon atmosphere were added diisopropyl ethyl amine (1.35 g, 10.50 mmol) and tert-butyl piperidin-4-ylcarbamate (1.7 g, 8.55 mmol) at RT. The reaction mixture was stirred at 150 C for 3 h. After consumption of the starting material (monitored by TLC), the reaction was diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified through silica gel column chromatography using 5% MeOH:DCM to afford tert-butyl (1 -(6-methylpyrimidin-4-yl) piperidin-4-yl) carbamate (1.75 g, 77%) as an off-white solid. ?H-NMR (DMSO-d6, 400 MHz): oe 8.34 (s, 1H), 6.69 (s, 1H),4.28-4.24 (m, 2H), 3.54-3.52 (m, 1H), 3.00-2.93 (m, 2H), 2.23 (s, 3H), 1.77-1.75 (m, 2H),1.38 (s, 9H), 1.30-1.22 (m, 3H); LC-MS: 293.3 (M+1); (column; X-Bridge C-18 (50 x 3.0 mm, 3.5 .im); RT 3.32 mm. 5 mM NH4OAc: ACN; 0.80 mL/min); TLC: 50% EtOAc:hexanes (R1: 0.2).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3435-25-4, its application will become more common.
Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66696; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia