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.1439-09-4, name is 5-Bromo-4-methylpyrimidine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.Recommanded Product: 1439-09-4
Example 277-(4-Methylpyrimidin-5-yl)-3-(pyrazin-2-yl)benzo[d]isoxazole [00184] A reaction flask was charged with tetrakis(triphenylphosphine)palladium(0) (4.45 mg, 3.85 muiotaetaomicron?), Preparation 25A (24.88 mg, 0.077 mmol), sodium carbonate (32.6 mg, 0.308 mmol), and 5-bromo-4-methylpyrimidine (13.99 mg, 0.081 mmol). The mixture was stirred at room temperature for 10 min under N2, then DME (Ratio: 2.0, Volume: 287 mu?), EtOH (Ratio: 1.000, Volume: 144 mu?), and water (Ratio: 1.000, Volume: 144 mu?) were added sequentially. The resultant mixture was heated at 90 C overnight. After 19 hr, the reaction mixture was allowed to cool to room temperature. The reaction was quenched with water. The reaction mixture was diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford a residue. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge CI 8, 19 x 250 mm, 5-muiotaeta particles; Guard Column: Waters XBridge CI 8, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5acetonitrile:water with 10-mM ammonium acetate; Gradient: 5-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The material was further purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5- muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient: 15- 50% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound (1.4 mg, 6.2%). ESI MS (M+H)+ = 290.0. HPLC Peak tr = 1.78 minutes. Purity >99%. HPLC Conditions: B.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1439-09-4, 5-Bromo-4-methylpyrimidine, and friends who are interested can also refer to it.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia