Category: 23631-02-9

Introduction of a new synthetic route about 4-Chloro-N,N-dimethylpyrimidin-2-amine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23631-02-9, 4-Chloro-N,N-dimethylpyrimidin-2-amine, and friends who are interested can also refer to it.

Electric Literature of 23631-02-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 23631-02-9, name is 4-Chloro-N,N-dimethylpyrimidin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of N-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine obtained in step B of example 1 (466 mg), (4-chloro-pyrimidin-2-yl)-dimethyl- amine (200 mg), and BuOH (1 mL) was stirred at reflux for 13 hr. The mixture was poured into saturated aqueous NaHC03 and the aqueous) layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromttography (NH-silica gel, 20% EtOAc in) to give N4-(cis-4-{[4-bromo-2-(trifluoromethoxy) benzyl] arnino}-cyclohexyl)-Na, N2- dimethylpyrimidine-2, 4-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure The residue was suspended in Et20 (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N4-(cis-4-{ [4-bromo-2-(trifluoromethoxy) benzyl]-amino} cyclohexyl)-N2, N2- dimethylpyrimidine-2, 4-diamine dihydrochloride (294 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDCI3) 8 1.42-1. 67 (m, 2 H), 2.03- 2.39 (m, 6 H), 2. 79-3.38 (m, 7 H), 4.13-4. 36 (m, 3 H), 6.89-7. 00 (m, 1 H), 7.42-7. 46 (m, 1 H), 7.50-7. 57 (m, 1 H), 7. 90-8. 01 (m, 1 H), 8.12 (d, J= 8.4 Hz, 1 H), 8.90-9. 00 (m, 1 H), 9.98-10. 18 (m, 2 H), 12.21-12. 37 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23631-02-9, 4-Chloro-N,N-dimethylpyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia