5-bromo-4-chlorothieno[2,3-d]pyrimidine
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![5-bromo-4-chlorothieno[2,3-d]pyrimidine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/a79ddfa4cd05409cbac783f4d323f44e.png "5-bromo-4-chlorothieno[2,3-d]pyrimidine")
5-bromo-4-chlorothieno[2,3-d]pyrimidine
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CAS No:
814918-95-1
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Formula:
C6H2BrClN2S
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Chemical Name:
5-bromo-4-chlorothieno[2,3-d]pyrimidine
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Synonyms:
5-bromo-4-chlorothieno[2,3-d]pyrimidine;Thieno[2,3-d]pyrimidine, 5-bromo-4-chloro-;5-bromo-4-chlorothieno [2,3-d] pyrimidine;PubChem18364;5-bromo-4-chloro-thieno[2,3-d]pyrimidine;SCHEMBL868188;bis(3-dimethylaminopropyl)amin;CTK5E8821;DTXSID10670293;BCP16930
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CAS No:
5-bromo-4-chlorothieno[2,3-d]pyrimidine Use and Manufacturing
To diisopropylamine (1.028 ml, 7.21 mmol, 1.8 equiv) in 10 mL THF at 0 °C was added n-butyl lithium (3.76 ml, 6.01 mmol, 1.5 equiv). After 1 h, the LDA solution was transferred to a solution of 6-bromo-4-chlorothieno[2, 3-d]pyrimidine (1.0 g, 4.01 mmol, 1.0 equiv) in 35 mL THF at -78 °C under nitrogen. The solution stirred for 1 h at -78 °C after which a mixture of 1.25 mL water and 5 mL THF was added slowly. The mixture was then warmed to 0 °C, poured into 60 mL water, and extracted with dichloromethane. The combined organic extracts were then dried over Na2SC> , filtered, and concentrated in vacuo to give a yellow solid which was chromatographed with 20percent EtOAc/Hexanes gradient elution to give 5-bromo-4-chlorothieno[2, 3-d]pyrimidine (671 mg, 67.1 percent yield) as a tan solid. NMR (400 MHz, chloroform- ) δ ppm 8.85 (s, 1 H), 7.64 (s, 1 H).Step 4: To a stirred solution of 6-bromo-4-chlorothieno[2, 3-c]pyrimidine (3 g, 12.048 mmol) in THF (120 mL) was added 2M LDA solution in THF/heptane/ethylbenzene (9 mL, 18.072 mmol) at -78 °C under nitrogen. The reaction mixture was stirred for 1 h at -78 °C, a mixture of 3.75 mL water and 15 mL THF was added slowly. The mixture was warmed to 0 °C, poured onto water (180 mL). The reaction mixture was extracted with dichloromethane (2 x 50 mL). The combined organic extracts were dried over NaLithium diisopropylamine (LDA) was prepared by addition of 2.5 molar BuLi (3.0 mL, 7.6 mmol) in hexanes to a ca. -50° C. solution of diisopropylamine (1.1 mL, 790 mg, 7.8 mmol) in anhydrous THF (15 mL). The solution was warmed to 0° C. for 10 min and then added dropwise to a solution of 6-bromo-4-chlorothieno[2, 3-d]pyrimidine (which was prepared as disclosed in WO 2003053446) (2.0 g, 8.0 mmol) in THF (30 mL) cooled to -100° C. The mixture was maintained at -90 to -100° C. for 45 minutes and then quenched with saturated aqueous NHTo a stirred solution of 6-bromo-4-chlorothieno[2, 3-c]pyrimidine (1 g, 4.0 mmol, 1 equiv) in THF (40 mL) was added 2M LDA in THF solution (3 mL, 6.0 mmol, 1.5 equiv) drop wise at -78 °C under nitrogen. The reaction was stirred for 1 h at -78 °C after which a mixture of water (1.25 mL) and THF (5 mL) was added slowly. The mixture was then warmed to 0 °C, poured onto water (60 mL), and extracted with DCM (2 x 30 mL). The combined organic extracts were combined and dried over Na
Computed Properties
Molecular Weight:249.52
XLogP3:3.2
Hydrogen Bond Acceptor Count:3
Exact Mass:247.88106
Monoisotopic Mass:247.88106
Topological Polar Surface Area:54
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-bromo-4-chlorothieno[2,3-d]pyrimidine
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