Electric Literature of 22325-27-5 ,Some common heterocyclic compound, 22325-27-5, molecular formula is C6H8N2S, 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.
Sodium hypochlorite (30.9 mL, 60.0 mmol) was added dropwise with rapid stirring to a solution of 4,6-dimethylpyrimidine-2-thiol (1.40 g, 10.00 mmol) and CaCl2 (14 g) in CH2Cl2 (60 mL) and 1N HCl (55.0 mL, 55.0 mmol) at -23 C. After the addition was complete, the mixture was stirred for 15 min at -23 C. and the phases where separated. The organic layer was transferred to a 250 mL 3-necked flask which was then chilled to -23 C. and equipped with a cold finger (-70 C.). NH3 was bubbled through the reaction mixture for 15 min. and then the reaction was slowly allowed to warm to rt and stirred 16 h. The resulting white precipitate was separated by filtration and the filtrate was concentrated under vacuum to yield 4,6-dimethylpyrimidine-2-sulfonamide (1.003 g, 5.36 mmol, 53.6% yield) as white solid. 1H NMR (300 MHz, acetone-d6) delta ppm 7.43 (s, 1H), 6.63 (br s, 2H), 2.53 (s, 6H). LC-MS retention time 0.39 min; m/z 188 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10 u C18 4.6¡Á50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22325-27-5, its application will become more common.
Reference:
Patent; Bristol-Myers Squibb Company; US2009/130057; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia