Introduction of a new synthetic route about 2-Chloro-4,6-dimethoxypyrimidine

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference of 13223-25-1 ,Some common heterocyclic compound, 13223-25-1, molecular formula is C6H7ClN2O2, 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.

2-Chloro-4,6-dimethoxypyrimidine (50 g, 0.29 mol) was suspended in trifluoroacetic anhydride (175 ml, 1.24 mol, 4 equiv.) and the mixture was cooled in a brine-ice bath to +2 0C. Concentrated nitric acid was then added drop-wise to the stirred mixture (CARE; effervescence and exotherm) at such a rate that the exotherm did not cause the temperature of the reaction mixture to rise above +40 0C (about 45 minutes). After 1 hour the reaction was complete (as determined by TLC of an aliquot which was quenched with water and extracted with DCM; plate eluted with DCM). The resulting thick white precipitate was poured onto ice (500 g) and the aqueous solution was extracted with dichloromethane (2 x 400 ml). The combined organic layers were then washed with saturated aqueous sodium bicarbonate solution (2 x 200 ml) until the washings remained at pH 7. The solution was dried (MgSO4) and the solvent was removed under reduced pressure to give a yellow- white crystalline solid. This material was partially dissolved in warm diethyl ether (~300ml) with stirring and then cooled in an ice-bath. Filtration gave the product as a pale yellow-white crystalline solid (56 g, 88 %).; 2-Chloro-4,6-dimethoxypyrimidine (2 g, 11.5 mol) was suspended in trifluoroacetic anhydride (3.2 ml, 23 mmol, 2 eq.) and the mixture was cooled in a brine ice-bath to +2 0C. Fuming nitric acid (0.58 ml, 13.8 mmol, 1.2 eq) was then added drop-wise to the stirred mixture (exotherm) at such a rate that the exotherm did not cause the temperature of the reaction mixture to rise above +40 0C (about 1 minute). The thick precipitate was then warmed to room temperature and left overnight. After this time the reaction was complete (as determined by TLC of an EPO aliquot which was quenched with water and extracted with DCM; TLC run with DCM and visualised with uv). Water (20 ml) was added to the resulting thick white precipitate and the aqueous solution was extracted with dichloromethane (2 x 40 ml). The combined organic layers were then washed with saturated aqueous NaHCO3 solution (-20 ml) until the washings remained at pH 7, dried (MgSO4) and the solvent was removed under reduced pressure to give a white crystalline solid (2.38 g, 95 %).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PARADIGM THERAPEUTICS LTD.; WO2007/582; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia