4,6-Dichloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidine

(2-methoxyphenyl)-2-(pyrimidin-2-yl)pyrimidin-4, 6-(1H, 5H)-dione (compound 1) to 4, 6-dichloro-5-(2-methoxyphenoxy)-2, 2'-bipyrimidine (compound 2); Charged 343.70 gm of phosphorous oxychloride followed by 175.0 gm of compound 1. Raised the temperature of reaction mass to reflux. Stirred the reaction mass at reflux for 4.0 hr. Reaction is monitored by HPLC. Cooled the reaction mass gradually to 40-50° C. Quenched the reaction mass slowly into 2.625 lit of water at 5-10° C. Stirred the reaction mass at 5-10° C. for 2.0 hrs. Filtered and washed the wet material thrice with 175.0 ml of water. Unloaded the wet material. Weight wet of Compound 2: 255 gm. Dried the wet material under vacuum at 55-60° C. for 8.0 hrs. Weight of dried compound 2: 182 gm (percent Yield: 93percent; HPLC Purity: >98percent))5- (2-methoxyphenoxy) -1H- [2, 2 '] - dipyridyl-4, 6-dione (IV) (30 g, 96 mmol)Toluene (400 mL), phosphorus pentachloride (44.0 g, 211.3 mmol) was added and heated to reflux for 2 h. The TLC reaction was complete. (3 mL), and the organic phase was combined, washed with saturated aqueous sodium carbonate solution (100 mL) and saturated brine (100 mL), and the organic phase was washed with water (100 mL) and saturated brine (100 mL) Dried over anhydrous sodium sulfate, and the residue was dried to obtain 29.0 g of the desired product 4, 6-dichloro-5- (2-methoxyphenoxy) -2, 2 '-bipyridine (V) 87percent.Step 4; 4, 6-dichloro-5-(2-methoxyphenoxy)-2, 2'-bipyrimidine: 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidine-4, 6(1H, 5H)-dione (804 mg, 2.6 mmol) was added to a mixture of phosphorous oxychloride (8 mL) and 2, 4, 6-trimethylpyridine (0.312 g, 2.6 mmol). Under continuous stirring, the mixture was heated at about 100° C. for about 16 hours, cooled to ambient temperature, poured onto ice-water, and concentrated in vacuo. The residue was diluted with water, the resulting precipitate was collected by filtration, and dried to give the title compound (776 mg, 86percent). Preparation of 4, 6- dichloro 5-(2-methoxyphenoxy) [2, 2]-bipyrimidinyl compound (formula-3)5 -(2 -methoxyphenoxy) [2, 2]-bipyrimidinyl diol (Formula-2) 4g (0.0128mol) was taken in acetonitrile (20mL) and Collidine(3.88g, 0.032mol). Phosphorous oxy chloride was added (19.64g, 0.128mol) slowly and refluxed for 5 to six hours, the reaction mass were quenched in water and the product was extracted in ethyl acetate. Organic layer was washed with water, sodium bicarbonate and saturated brine and dried over anhydrous sodium sulphate and concentrated. The concentrated reaction mass was isolated using n-heptane and the obtained solid was dried under vacuum yielding 3.4g of slightly brown solid 4, 6- dichloro 5-(2- methoxyphenoxy) [2, 2]-bipyrimidinyl compound (formula-3) (99percent) having the X-ray diffraction pattern with peaks at 8.547, 9.867, 11.068, 11.97, 13.851, 14.726, 15.539, 17.213, 18.428, 20.463, 22.232, 22.704, 23.536, 23.937, 24.827, 26.291, 26.545, 27.294, 27.815, 28.223, 29.278, 30.022, 30.5, 31.447, 31.996, 32.454, 33.43, 33.644, 34.251, 34.89, 35.662, 36.393, 37.402, 38.523, 39.022, 40.238, 40.724, 41.35, 41.93, 43.732, 44.289, 45.24, 47.267, 47.978, 49.123, 49.438, 50.22, ± 0.2 degrees two theta values.5-(2-methoxyphenoxy) [2, 2]-bipyrimidinyl diol (Formula-2) 4 g (0.0i28 mol) was taken in acetonitrile (20 mL) and Collidine (3.88 g, 0.032 mol). Phosphorous oxy chloride was added (i9.64 g, 0.i28 mol) slowly and refluxed for 5 to six hours, the reaction mass were quenched in water and the product was extracted in ethyl acetate. Organic layer was washed with water, sodium bicarbonate and saturated brine and dried over anhydrous sodium sulphate and concentrated. The concentrated reaction mass was isolated using n-heptane and the obtained solid was dried under vacuum yielding 3.4 g of slightly brown solid 4, 6- dichloro 5-(2- methoxyphenoxy) [2, 2] -bipyrimidinyl compound (formula- 3) (99percent) having the X-ray diffraction pattern with peaks at8.547, 9.867, 11.068, 11.97, 13.851, 14.726, 15.539, 17.213, 18.428, 20.463, 22.232, 22.704, 23.536, 23.937, 24.827, 26.291, 26.545, 27.294, 27.815, 28.223, 29.278, 30.022, 30.5, 31.447, 31.996, 32.454, 33.43, 33.644, 34.251, 34.89, 35.662, 36.393, 37.402, 38.523, 39.022, 40.238, 40.724, 41.35, 41.93, 43.732, 44.289, 45.24, 47.267, 47.978, 49.123, 49.438, 50.22, ±0.2 degrees two theta values.In a dry, IL round bottom flask, 70 g 4, 6-dihydroxy-5-(2-methoxy phenoxy)[2, 2'] bipyrimidine (0.22 mol) was taken. To this 90.73 g triethylamine (0.89 mole) was added and mixture was stirred, subsequently 137.4 g phosphorous oxychloride (0.89 mole) was added. Thick mass was obtained and subsequently the reaction mixture was stirred at 90-95

Molecular Weight:349.2
XLogP3:3.6
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:348.0180810
Monoisotopic Mass:348.0180810
Topological Polar Surface Area:70
Heavy Atom Count:23
Complexity:361
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes