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CAS No. : | 55084-66-7 | MDL No. : | MFCD12545984 |
Formula : | C6H4Cl2N2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NMFCRGDGVPCDHH-UHFFFAOYSA-N |
M.W : | 223.08 | Pubchem ID : | 18969078 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 1759 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With thionyl chloride In N,N-dimethyl-formamide for 1 h; Heating / reflux | A slurry of potassium trimethylsilyl oxide (90percent tech., 40 g, 0.31 mol) in 1,2-dimethoxyethane (300 mL) was added, slowly over 20 min, to a solution of ethyl-4-chloro-2-methylthio-5-pyrimidinecarboxylate (Aldrich, 15 g, 64 mmol) in 1,2-dimethoxyethane (100 mL). Said addition, being mildly exothermic, may warrant the use of an ice bath to maintain ambient temperature conditions during addition. After addition was complete, the resulting suspension was stirred at ambient temperature for 1 h, then warmed to reflux for 36 h, then allowed to cool to ambient temperature. Reaction mixture was quenched with 1 M HCl(aq), then extracted with ethyl acetate and dried using sodium sulfate to produce a crude solid (11 g). Said crude solid was then recrystallized in ethyl acetate to afford 4-hydroxy-2-methylsulfanylpyrimidine-5-carboxylic acid as a white solid (8.8 g, 47 mmol, 73percent yield). MS (-ESI) m/z 185 (M-, 100). An aliquot of this material (3.00 g, 16.1 mmol) was diluted with thionyl chloride (90 mL) followed by DMF (0.20 mL) and the resulting solution was warmed to reflux. After 1 hour at reflux, the solution was allowed to cool to ambient temperature and was concentrated in vacuo to afford a beige solid which was triturated once from hot toluene and then once again from hot hexanes (i.e., in both instances the soluble material was the desired fraction). This afforded, after concentration in vacuo, the titled compound as a white solid (3.90 g, 15.6 mmol, 97percent yield). 1H NMR (300 MHz, CDCl3) δ 9.15 (s, 1H), 2.63 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methylmagnesium bromide; In tetrahydrofuran; | (1) Preparation of intermediate (II) 5,8-dihydro-2-methanesulfonyl-5-oxo-8-(2-thiazolyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester A solution of malonic acid monoethyl ester (12.3 g) dissolved in tetrahydrofuran (80 ml) was cooled with ice, and then, to the resulting solution, a solution of methylmagnesium bromide (3M) in ether (64 ml) was added dropwise. After the resultant mixture was stirred for 20 minutes, a solution of <strong>[55084-66-7]2-methylthio-4-chloropyrimidine-5-carbonylchloride</strong> (8.6 g) dissolved in tetrahydrofuran (100 ml) was added dropwise to the mixture, which was then stirred for two hours at a room temperature. This reaction mixture was poured into ice water, and then, concentrated hydrochloric acid was added to the resulting solution so that pH might be adjusted to be 5-6, and the solution was subsequently extracted with ethyl acetate. The obtained extract was dried over anhydrous sodium sulfate, and solvent was distilled off under reduced pressure. Then, purification was conducted by silica gel column chromatography (eluent: chloroform), and thus, 3-(2-methylthio-4-chloropyrimidin-5-yl)-3-oxopropionic acid ethyl ester (8.0 g) was obtained. IR (neat) cm-1: 1743 MS (m/z): 275 (MH+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.25h; | To a mixture of <strong>[55084-66-7]4-chloro-2-methylsulfanylpyrimidine-5-carbonyl chloride</strong> prepared above (113 mg, 0.54 mmol) in dichloromethane was added 4-fluoroaniline (56 muL, 0.59 mmol). This was followed by the dropwise addition of DIPEA. The mixture was stirred for 15 min, the mixture was diluted with dichloromethane, washed with water and saturated aqueous sodium bicarbonate and was dried over sodium sulfate. Filtration and concentration afforded a residue that was purified by trituration from ethyl acetate with hexanes. The resulting off-white solid (122 mg, 0.41 mmol, 76%) was sufficiently pure to use without further purification. 1H NMR (300 MHz, DMSO-d6) delta 10.7 (s, 1H), 8.86 (s, 1H), 7.69 (m, 2H), 7.23 (m, 2H), 2.56 (s, 3H); MS (EI) m/z 296.2 (M-H)-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With thionyl chloride; N,N-dimethyl-formamide; at 90℃; for 3h; | The <strong>[397308-78-0]4-hydroxy-2-(methylthio)pyrimidine-5-carboxylic acid</strong> (35.8 g, 192 mmol) was treated with 500 mL of thionyl chloride and 0.75 mL of DMF. The mixture was stirred at 90 C for 3 hrs. After cooling to ambient the mixture was concentrated, re-dissolved in hot toluene (~50 mL) and the unsoluble particle filtered. The filtrate was concentrated to give 4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride (42.46 g, 190 mmol, 99 % yield) as a white solid.1H NMR (300 MHz, DMSO-d6) delta 8.99 (s, 1H), 2.58 (s, 3H). |
97% | With thionyl chloride; In N,N-dimethyl-formamide; for 1h;Heating / reflux; | A slurry of potassium trimethylsilyl oxide (90% tech., 40 g, 0.31 mol) in 1,2-dimethoxyethane (300 mL) was added, slowly over 20 min, to a solution of ethyl-4-chloro-2-methylthio-5-pyrimidinecarboxylate (Aldrich, 15 g, 64 mmol) in 1,2-dimethoxyethane (100 mL). Said addition, being mildly exothermic, may warrant the use of an ice bath to maintain ambient temperature conditions during addition. After addition was complete, the resulting suspension was stirred at ambient temperature for 1 h, then warmed to reflux for 36 h, then allowed to cool to ambient temperature. Reaction mixture was quenched with 1 M HCl(aq), then extracted with ethyl acetate and dried using sodium sulfate to produce a crude solid (11 g). Said crude solid was then recrystallized in ethyl acetate to afford <strong>[397308-78-0]4-hydroxy-2-methylsulfanylpyrimidine-5-carboxylic acid</strong> as a white solid (8.8 g, 47 mmol, 73% yield). MS (-ESI) m/z 185 (M-, 100). An aliquot of this material (3.00 g, 16.1 mmol) was diluted with thionyl chloride (90 mL) followed by DMF (0.20 mL) and the resulting solution was warmed to reflux. After 1 hour at reflux, the solution was allowed to cool to ambient temperature and was concentrated in vacuo to afford a beige solid which was triturated once from hot toluene and then once again from hot hexanes (i.e., in both instances the soluble material was the desired fraction). This afforded, after concentration in vacuo, the titled compound as a white solid (3.90 g, 15.6 mmol, 97% yield). 1H NMR (300 MHz, CDCl3) delta 9.15 (s, 1H), 2.63 (s, 3H). |
83.59% | With thionyl chloride; In N,N-dimethyl-formamide; at 100℃; for 2h; | To a stirred solution of 9 <strong>[397308-78-0]4-hydroxy-2-(methylthio)pyrimidine-5-carboxylic acid</strong> (2.5 g, 13.44 mmol, 1 eq) in 47 DMF (2.5 mL) was added 825 SOCl2 (10 mL) and the resultant mixture was heated at 100 C. for 2 h. After completion, the mixture was cooled to RT was then concentrated in vacuo to give 826 4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride (2.65 g, 83.59%) as an off-white solid. (0870) LCMS: 224 [M+1]+ |
With thionyl chloride; at 80℃; for 18h; | In a 250mL round bottom flask with magnetic stir bar, 4-hydroxy-2- (methylsulfanyl)pyrimidine-5-carboxylic acid (12 g, 64.45 mmol, 1.00 eq.) was suspended in thionyl chloride (120 mL). The resulting solution was stirred for 18 h at 80 C, and then concentrated under reduced pressure to afford the acid chloride intermediate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at -78 - 20℃; for 3h;Inert atmosphere; | An oven dried flask, equipped with stir bar and septa, was charged with <strong>[55084-66-7]4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride</strong> (Aaron Chemistry, 1338 mg, 6 mmol). The flask was capped with septa, evacuated and backfilled with nitrogen (three times). The solid was dissolved in tetrahydrofuran (24.0 mL), cooled to -78 C. and kept under nitrogen. (2-Chlorobenzyl)magnesium chloride (14.40 mL, 7.20 mmol) was then slowly added. After the addition was completed, the dry ice/acetone bath was removed and the mixture was stirred at ambient temperature for 3 hours. The mixture was quenched with aqueous 1 M HCl (50 mL), extracted with ethyl acetate (3*80 mL) and the combined extracts were washed with brine, dried over magnesium sulfate (MgSO4), filtered and concentrated. The crude product obtained was purified by flash chromatography (Isco, Redi-Sep column, 0-30% ethyl acetate/hexane, linear gradient) to afford the title compound. 1H NMR (300 MHz, CDCl3) delta ppm 8.72 (s, 1H), 7.47-7.36 (m, 1H), 7.36-7.21 (m, 3H), 4.41 (s, 2H), 2.61 (s, 3H); MS (ESI) m/z 313 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Step 1:Preparation of the CuCN·2LiCl solution.To a 250 mL round bottom flask was added copper(I) cyanide (8.95 g, 100 mmol) and lithium chloride (8.48 g, 200 mmol).The flask was capped with septa and heated under high vacuum at 140C for 3 hours.After cooling to ambient temperature, dry tetrahydrofuran (90 mL) was added and the mixture stirred until the salts were dissolved (24 hours) to give a ~1 Msolution.Step 2: Organozinc addition.To a 1.0 M solution of CuCN:2LiCl (96 mL, 96 mmol) at -25C was slowly added a 0.5 M solution of (2,6-dichlorobenzyl)zinc(II) chloride (192 mL, 96 mmol).The resulting reaction mixture was stirred for 15 minutes at this temperature.This solution was added over 10 minutes to a stirring solution of the <strong>[55084-66-7]4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride</strong> (7, 17.85 g, 80 mmol) in 160 mL of dry tetrahydrofuran via cannula.After the addition was complete, the bath was removed and the mixture was stirred at ambient temperature under nitrogen for 1.5 hours.The mixture was quenched with 400 mL of saturated aqueous sodium bicarbonate and after stirring vigourously for 15 minutes, the mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. The ssolid obtained was recrystalyzed (EtOAc/heaxane) and the filtrate was purified by flash chromatography on a CombiFlash Teledyne Isco system using a Teledyne Isco RediSep Rf gold 220 g silica gel column (eluting 0-30% EtOAc/Hept) to give an additional amount of the title compound. Obtained a total of 21.98 g of final product (79% yield).1H NMR (300 MHz, CDCl3)deltappm 8.79 (s, 1H), 7.41 - 7.31 (m, 2H), 7.25 - 7.16 (m,J= 8.8, 7.3, 1H), 4.68 (s, 2H), 2.63 (s, 3H); MS (ESI) m/z 347 (M+H)+. | |
Step 1: Preparation of the CuCN.2LiCl solution. [0302] To a 250 mL round bottom flask was added copper(I) cyanide (8.95 g, 100 mmol) and lithium chloride (8.48 g, 200 mmol). The flask was capped with septa and heated under high vacuum at 140 C. for 3 hours. After cooling to ambient temperature, dry tetrahydrofuran (90 mL) was added and the mixture stirred until the salts were dissolved (24 hours) to give a ?1 M solution. Step 2: Organozinc Addition. [0303] To a 1.0 M solution of CuCN:2LiCl (64.6 ml, 64.6 mmol) at -25 C. was slowly added a 0.5 M solution of (2,6-dichlorobenzyl)zinc(II) chloride (129 ml, 64.6 mmol). The resulting reaction mixture was stirred for 15 minutes at this temperature. This solution was added over 10 minutes to a stirring solution of the <strong>[55084-66-7]4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride</strong> (12 g, 53.8 mmol) in 110 mL of dry tetrahydrofuran via cannula. After the addition was complete, the bath was removed and the mixture was stirred at ambient temperature under nitrogen for 1.5 hours. The mixture was quenched with 200 mL of saturated aqueous sodium bicarbonate and after stirring vigorously for 15 min, the mixture was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude material was purified by flash chromatography (Isco, Redi-Sep column, 0-30% ethyl acetate/hexane) to give an additional amount of the title compound. 1H NMR (300 MHz, CDCl3) delta ppm 8.79 (s, 1H), 7.41-7.31 (m, 2H), 7.25-7.16 (m, J=8.8, 7.3, 1H), 4.68 (s, 2H), 2.63 (s, 3H); MS (ESI) m/z 347 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With ammonia; In 1,4-dioxane; water; | The acid chloride prepared above was dissolved in dioxane (10 mL), which was added dropwise to NH3.H20 (100 mL) slowly at 0 C. Precipitation happened, and then the solids were collected by filtration and the solid was dried in a JR dryer to yield 8 g (6 1%) of 4-chloro- 2-(methylsulfanyl)pyrimidine-5-carboxamide as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.7% | With pyridine; In dichloromethane; at 0 - 20℃; for 48h; | To a solution of 2,6-dichloroanillne (41.02 g, 253 mmol) and pyridirie (25.03 g, 316 mmcl) in CH2CI2 (400 mL) a solution of 4-chloio-2-(mehylthio)pyrimidine-5-carbonyl chloride (56 5 g, 253 mrnol) in CH2CI2 (400 mL) was added dropwise at 0 C. The reaction mixture was stirred at RT for 2 days, the solvent was evaporated in vacuc and the remaining residuewas washed with water twice, followed by 10% sq. HCI and water. The crude product was purified by recrystallization from EtOH to give 67,7 g (76.7 %) of the title compound as a white solid. LCMS (Method B): RT = 1.53 mm, mix = 348/350 [M+H1. |
42% | With Amberlyst A21; In ethyl acetate; at 40℃;Inert atmosphere; | A mixture of 4-chloro-2- (methylthio) pyrimidine-5-carbonyl chloride (35 g, 157 mmol) and Amberlyst A21 (6 g, 149 mmol) in ethyl acetate (250 mL) was heated to 40 C followed by the dropwise addition of a solution of 2,6-dichloroaniline (24.21 g, 149 mmol) in ethyl acetate (250mL) . The reaction mixture was heated at 40 C under a nitrogen atmosphere overnight. The resulting suspension was allowed to cool to room temperature and filtered. The isolated solids were taken up in hot tetrahydrofuran (100 mL) and filtered, repeating the process with theundissolved solid a further two times until most of the solid was dissolved. The combined filtrates were concentrated to dryness under reduced pressure to give a pale yellow solid. This was slurried in dichloromethane (100 mL) to give the title compound as a white solid(22.1 g, 42%) . ?H NMR (300 MHz, DMSO-d6) : 3 10.71 (s, 1H),8.82 (s, 1H), 7.62 (d, 2H), 7.43 (t, 1H), 2.60 (s, 3H) LCMS (Method C) : = 1.46 mm, m/z = 348 [M+H]. |
With triethylamine; In dichloromethane; at 20℃; for 2h;Inert atmosphere; | To a stirred solution of 296 2,6-dichloroaniline (9.07 g, 56 mmol, 1 eq), in dry 743 DCM (60 mL) 155 Et3N (23.43 mL, 168.1 mmol, 3 eq) was added followed by addition of 826 <strong>[55084-66-7]4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride</strong> (12.5 g, 56 mmol, 1 eq) in DCM (60 mL) under stirring under inert atmosphere. The resulting solution was stirred at rt for 2 h. The progress of the reaction was monitored by LCMS. After complete consumption of starting material, the reaction mass was diluted with water (50 mL) and extracted with DCM (50 mL×3). The combined organic layer was dried over Na2SO4, concentrated to afford 829 4-chloro-N-(2,6-dichlorophenyl)-2-(methylthio)pyrimidine-5-carboxamide (12.0 g, 61%) which was used without further purification. (0808) LCMS: 348 [M+1]+ |
Tags: 55084-66-7 synthesis path| 55084-66-7 SDS| 55084-66-7 COA| 55084-66-7 purity| 55084-66-7 application| 55084-66-7 NMR| 55084-66-7 COA| 55084-66-7 structure
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P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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