2-METHYLTHIO-4-BROMOPYRIMIDINE
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2-METHYLTHIO-4-BROMOPYRIMIDINE
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CAS No:
959236-97-6
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Formula:
C5H5BrN2S
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Chemical Name:
2-METHYLTHIO-4-BROMOPYRIMIDINE
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Synonyms:
4-broMo-2-(Methylsulfanyl)pyriMidine;4-BroMo-2-(Methylthio)pyriMidine, 95+%;2-METHYLTHIO-4-BROMOPYRIMIDINE;4-Bromo-2-(methylthio)pyrimidine;Pyrimidine, 4-bromo-2-(methylthio)-
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CAS No:
Safety Information
8
|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-METHYLTHIO-4-BROMOPYRIMIDINE Use and Manufacturing
Bromo trimethylsilane (23 mL, 174.31 mmol) was addedto a solution of 4-chloro-2-methylsulfanylpyrimidine (2.9 g 25 mmol) inacetonitrile (240 mL).The mixture was stirred for 30 h at 40°C. The reactionwas monitored by TLC. After cooling to room temperature, NaHCOTo a stirred solution of 2-(methylthio)pyrimidin-4(3H)-one (5 g, 35.21 mmol, leq) in ACN (lOOmL) was added POBrTo a stirred solution of 2-(methylthio)pyrimidin-4(3H)-one (5 g, 35.21 mmol, leq) in ACN (lOOmL) was added POBr3 (12.1 g, 42.3 mmol, 1.2 eq) at RT, then the reaction mixture was heated to 80°C for 5h. Monitored by TLC, the reaction mixture was cooled to RT and quenched in ice cold water then extracted with EtOAc (2X100mL). The combined organic layer was dried over Na2SC>4 and concentrated to crude compound. The crude compound was purified by column chromatography (silica gel, 100-200 mesh) using 0-10percent EtOAc in pet ether as eluent to afford 4- bromo-2-(methylthio)pyrimidine (6g, 83percent) as off-white solid. LCMS: [M+H]+ 204.9.General procedure: In two neck 50 mL round bottom flask dry under nitrogen ethylN-imidazo[1, 2-b]pyridazin-6-ylcarbamate (0.104 g, 0.66 mmol) was placed inanhydrous toluene (2.1 mL). After 10 min, 3-bromopyridin (0.083 mL, 0.66 mmol), Pd(OAc)2 (0.045 g, 10%), triphenylphosphine(0.035 g, 20%), was added and then K2CO3 (0.184 g, 1.29mmol). The mixture was heated at 110C during 8 h. After cooling to roomtemperature, the solvent was evaporated. The crude residue was diluted in AcOEtand washed with NaCl solution. The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purifiedby chromatography on silica gel using Cyclohexane-AcOEt (7:3). Evaporation ofthe eluent in vacuum gave the desired compound in 6.8% yield (0.013 g) as awhite powder.
Computed Properties
Molecular Weight:205.08
XLogP3:2.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:203.93568
Monoisotopic Mass:203.93568
Topological Polar Surface Area:51.1
Heavy Atom Count:9
Complexity:91
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Business licensed Certified factoryManufactory Supplier of Active Pharm Ingredients,Chemical Catalyst,Pharmaceutical Intermediates,Flavors and Fragrances,Agrochemicals,Chemical Pesticides,Organic Intermediates,OLED IntermediatesInquiryCAS No.: 959236-97-6Grade: Pharmaceutical GradeContent: 99%
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