With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.56621-90-0, name is 5-Amino-2-chloropyrimidine, molecular formula is C4H4ClN3, molecular weight is 129.5477, as common compound, the synthetic route is as follows.Quality Control of 5-Amino-2-chloropyrimidine
To a solution of triphosgene (1.38 g, 4.65 mmol) in Ethyl acetate (20 ml) at 0 C. a solution of 2-chloro-5-aminopyrimidine (1 g, 7.75 mmol)/DIPEA (8 ml, 4.65 mmol) in ethyl acetate (40 ml) was slowly added (20 minutes) and the reaction mixture was stirred for 15 minutes at the same temperature. Maintaining the reaction mixture at 0 C., vacuum was applied (10 minutes) for removing the excess of phosgene. A solution of DMAP (0.945 g, 7.75 mmol) in ethyl acetate/dichloromethane 1:1 (8 ml) was added and the reaction mixture was stirred for 5 minutes at the same temperature. A solution of methyl (R)-2-amino-2-methyl-butyrate hydrochloride (2.59 g, 15.5 mmol) in ethyl acetate (30 ml) was slowly added (15 minutes) at 0 C. and the reaction mixture was stirred for 30 minutes at the same temperature. The reaction was quenched with aqueous buffer (pH3) while the pH was allowed to reach 5-6 and two phases were separated. The organic layer was washed with aqueous buffer (pH3) (2×20 ml) and then brine (20 ml), dried (Na2SO4), filtered and evaporated affording the urea intermediate as orange foam. The urea was dissolved in MeOH (20 ml), NaOMe (0.41 g, 7.75 mmol) was added and the reaction mixture was stirred for 15 minutes at r.t. The mixture was quenched with an aqueous saturated solution of ammonium chloride (25 ml) and diluted with ethyl acetate (50 ml). Two phases were separated and the organic layer was washed with brine (2×20 ml), dried (Na2SO4), filtered and evaporated. The residue was triturated with Et2O (10 ml) and the solid collected affording the title compound (1.22 g) as a beige solid. LC/MS: QC-3_MIN: Rt=1.341 min; 255 [M+H]+.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,56621-90-0, 5-Amino-2-chloropyrimidine, and friends who are interested can also refer to it.
Reference:
Patent; Alvaro, Giuseppe; Marasco, Agostino; US2014/323508; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia