(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Crystalline solid

In a 50ml three-necked flask with magnetic stirring, Add 20ml of dichloromethane and 4, 6-dichloro-5-allylpyrimidine(5.0 g, 0.026 mol), followed by the addition of dimethyl sulfoxide (8 g, 0.104 mol) and triethylamine (5.5 mL, 0.040 mol).Cool to -40 ° C, pass O3 until the reaction solution turns blue, Stop using O3 and switch to N2 for 30 minutes.Exclude O3 in the system.Add thiourea (2.0 g, 0.026 mol) and naturally raise to room temperature.Starch potassium iodide test paper detection (unchanged blue), Ensure that no peroxide is present in the reaction system. Add 60ml of water, The mixture was extracted twice with methylene chloride.The yield was 88percent.Step 3 - Synthesis of compound ID; Compound 1C (9.73 g, 51.47 mmol) was dissolved in an acetone: water (1:1, 290 mL) mixture and to the resulting solution was added potassium osmate dihydrate (0.64 g, 1.75 mmol). The resulting reaction was allowed to stir for about 5 minutes, then solid sodium periodate (44 g, 205, 37 mmol) was added in 4 portions over 1 hour, ensuring that the reaction temperature did not exceed 40 Step 3 - Synthesis of Compound ID; Compound 1C (9.73 g, 51.47 mmol) was dissolved in a mixture of acetone: water (1 :1, 290 mL) and to the resulting solution was added potassium osmate dihydrate (0.64 g, 1.75 mmol). The resulting mixture was allowed to stir for about 5 minutes, then sodium periodate (44 g, 205.37 mmol) was added in 4 portions over a 1 hour period, during which time the temperature of the reaction did not exceed 40 Step 3 - Synthesis of Compound ID; Compound 1C (9.73 g, 51.47 mmol) was dissolved in a mixture of acetone: water (1:1, 290 mL) and to the resulting solution was added potassium osmate dihydrate (0.64 g, 1.75 mmol). The resulting solution was allowed so stir for 5 minutes, then solid sodium periodate (44 g, 205.37 mmol) was added in 4 portions over a 1 hour period. The temperature of the reaction didn't exceed 40Compound 1B (9.73 g, 51.47 mmol) was dissolved in an acetone: water (1 :1 , 290 mL) mixture and to the resulting solution was added potassium osmate dihydrate (0.64 g, 1.75 mmol). The reaction was allowed to stir for 5 minutes, then solid sodium periodate (4 4g, 205.37 mmol) was added in 4 portions over a 1 hour period, during which time, th reaction temperature did not exceed 40 °C. The resulting suspension was was allowed to stir at room temperature for x hours for 1 hour, during which time the reaction mixture was permitted to cool to room temperature on its own. The reaction mixture was then filtered and the filtrate was concentrated in vacuo to remove acetone. The remaining aqueous layer was extracted with dichloromethane (2 x 200 mL) and the combined organic layers were washed with 10percent sodium thiosulfate solution, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide Compound 1C (8.16 g, 83.01percent), which was used without further purification.A solution of compound 4 (100 g, 0.53 mol) in MeOH (400 ml) and CH2Cl2 (150 ml) was cooled to –40°C, and ozone was bubbled through the mixture for 2 h. Then the reaction mixture was purged with nitrogen for 20 min to remove the excessive ozone. Thiocarbamide (40 g, 0.53 mol) was added to the mixture and stirred for 1 h until the starch-KI paper did not turn blue. The solvent was distilled off, the residue was extracted with CH2Cl2 (300 ml) and washed with water (2×100 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue that was triturated with petroleum ether (200 ml). Yield 76.8 g (76percent), white solid, mp 88–90°C (mp 89–91°CStep 1 : (4, 6-Dichloro-5-pyrimidinyl)acetaldehyde (209)To a stirred solution of 4, 6-dichloro-5-(2-propen-1-yl)pyrimidine (2, 274 g, 1.45 mol) in 1 :1 acetone-HStep 4:To a stirred solution of 5-allyl-4, 6-dichloropyrimidine (2.5 g) in dry dioxane (25 mL), N-methyl morpholine N-oxide (2.3 g) and osmium tetroxide (0.85 mL, 25percent solution in water) were added. The reaction mixture was stirred at room temperature for 2 hours before being quenched by solid sodium bisulphate. The reaction mixture was filtered through celite bed. The celite bed was washed with dioxane (10 mL). The combined filtrate was taken into a 100 mL three necked round bottom flask and sodium metaperiodate (6 g, in 5mL water) was added. The reaction mixture was stirred at room temperature for about 3 hours, then diluted with water (30 mL). Aqueous layer was extracted with dichloromethane (2 x 25 mL). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na[0108] 5-Allyl-4

Molecular Weight:191.01
XLogP3:1.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:189.9700681
Monoisotopic Mass:189.9700681
Topological Polar Surface Area:42.8
Heavy Atom Count:11
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes