| 92% |
With sulfuryl dichloride; In acetic acid; |
Referential Example 1 Synthesis of 5-chloro-<strong>[18592-13-7]6-chloromethyluracil</strong> To a suspension of <strong>[18592-13-7]6-chloromethyluracil</strong> (163 g) in acetic acid (500 ml), sulfuryl chloride (120 ml) was added dropwise at room temperature over 20 minutes, followed by stirring at the same temperature for 3 hours. The reaction mixture was poured into ice water (500 ml), and a crystallized matter was collected by filtration, whereby 182.3 g of the title compound were obtained (yield: 92%). Melting point: 225 C. min. (decomposed). NMR spectrum (DMSO-d6) delta: 4.46(2H,s), 11.57(1H,s), 11.71(1H,s). |
| 66% |
With sulfuryl dichloride; acetic acid; at 30 - 35℃; |
To 20.0g 6 - chloro methyl uracil is added in 100 ml acetic acid, stirring 20 minutes into the 22 ml chloride, dropwise, 30 - 35 C stirring reaction, TLC monitoring raw material of reaction, the reaction liquid slowly putting into 200 ml ice water, filtered, 10 - 15ml methanol washing, 50 C drying by blowing, getting white solid 16.0g, yield 66.0%. |
|
With sulfuryl dichloride; In acetic acid; at 20℃; |
50 g of <strong>[18592-13-7]6-chloromethyluracil</strong>, 150 ml of acetic acid was charged into a 250 ml flask, adding 38 ml of sulfonyl chloride dropwise at room temperature with stirring, TLC detection of the raw material indicated it was completely consumed, 200 ml of water was added dropwise under an ice bath, after filtration, the white solid was collected by filtration and the filter cake was washed three times with 30 ml each time and dried at 50 C to obtain a white intermediate I crude product of 54.0 g, yield 88.6%. |
|
With thionyl chloride; acetic acid; at 20 - 30℃; for 6h;Cooling with ice; |
In a 20 L reaction flask, compound SM1 (1000.0 g, 6.23 mol) was added to 5000 mL of acetic acid. Mechanical stirring was started and an ice bath was added. Sulfonyl chloride (1000 mL, 12.37 mol) was added dropwise keeping the temperature of the addition below 30 C. Canada completed at room temperature (20 ) reaction 6h, a large number of white solid precipitation. TLC trace compound SM1 point reaction disappeared (dichloromethane: methanol = 10: 1), the reaction was completed. The reaction mixture was suction filtered, and the resulting solid was air-dried for 12 hours at 60 C to give 5-chloro-<strong>[18592-13-7]6-chloromethyluracil</strong>. |
| 180 g |
With sulfuryl dichloride; acetic acid; at 15 - 30℃; for 7h;Inert atmosphere; |
Sulfuryl chloride (302 ml) was slowly added to a pre-cooled mixture of 6- (chloromethyl)pyrimidine-2,4(1H,3H)-dione compound of formula-2a (200 gm) and acetic acid (1400 i-ni) at 15-20C under nitrogen atmosphere. Raised the temperature of the reaction mixture to 25-30C and stined for 7 hrs at same temperature. Filtered the solid, washed with ethyl acetate and suck dried the material to get the title compound.Yield: 180 gm. |
| 10.1 g |
|
Synthesis of 5-chloro-6-(chloromethyl)- l,2,3,4-tetrahydropyrimidine-2,4-dione: Into a 1- L round-bottom flask, was placed 6-(chloromethyl)- l,2,3,4-tetrahydropyrimidine-2,4-dione (15 g, 93.42 mmol, 1 equiv), acetic acid (225 mL), acetyl acetate (15 mL). The resulting solution was stirred for 30 min at 80 C in an oil bath. Then NCS (16.2 g, 121.32 mmol, 1.30 equiv) was added at 60 C. The resulting solution was stirred for 3h at 60 C in an oil bath. The reaction was then quenched by the addition of 500 mL of water/ice. The solids were collected by filtration. The solid was dried in an oven under reduced pressure. This resulted in 10.1 g of 5- chloro-6-(chloromethyl)- l,2,3,4-tetrahydropyrimidine-2,4-dione as an off-white solid. LC-MS- BLV-CY-202- 1 : (ES, m/z): 195[M+H]+. H-NMR- BLV-CY-202- 1 : (300 MHz, OMSO, ppm): delta 11.71 (s, 1H), 11.56 (s, 1H), 4.47 (s, 2H). |
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