5-Bromouridine

WHITE FINE POWDER

5-Bromouridine (BrUrd) is a uridine derivative with a bromo substituent at the fifth carbon. BrUrd is incorporated into RNA and can be detected immunocytochemically and analysed by cytometry. It causes DNA damage through base substitution and increases the number of mutations.

5-bromouridine is a uridine having a bromo substituent at the 5-position. It has a role as a mutagen.

General procedure: 2'-O-Methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile solution(H2O:CH3CN 1:9, 5 mL) under stirring. NaN3 (0.104 g, 1.6 mmol) was added, followed by addition of SMBI (0.101 g, 0.44 mmol) at r.t. and the mixture was stirred. Progress of the reaction was followedby TLC. On completion of the reaction after 1.5 h, the reaction mixture was filtered, evaporated todryness under reduced pressure and coevaporated with acetonitrile (2 × 2 mL). The crude reactionmixture was purified by column chromatography (4percent–6percent MeOH in DCM, v/v) to afford bromonucleoside 6 (0.117 g, 93percent) in pure form as a white solidTypical procedure for the bromination of unprotected nucleosides: DBH (323 mg, 1.13 mmol) was added to a stirred solution of 1d (500 mg, 2.05 mmol) in DMF (5 mL). The resulting pale-yellow solution was stirred at room temperature for 20 minutes or until TLC showed absence of starting material and formation of less polar product. Volatiles were evaporated and the residue was coevaporated with MeCN. The resulting pale solid was crystallized from hot acetone to give 2d (500 mg, 75percent) as colorless crystals with data as reported.To a solution of uridine 146 (20.0 g, 82mmol) and N BS (21 .7 g, 0.12 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide, then the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was added. After evaporation of the solvent, the residue was precipitation with methanol to give 22.0 g compound 147 as light yellow solid.Synthesis of Compound 147: To a solution of uridine 146 (20.0 g, 82mmol) and NBS (21 .7 g, 0.12 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide, then the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was added. After evaporation of the solvent, the residue was precipitation with methanol to give 22.0 g compound 147 as light yellow solid.Synthesis of Compound 1 47: To a solution of uridine 146 (20.0 g, 82mmol) and NBS (21 .7 g, 2 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide, n the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was ded. Afte ompound 1Synthesis of Compound 147: To a solution of uridine 146 (20.0 g, 82mmol) and NBS (21.7 g, 0.12 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide, then the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was added. After evaporation of the solvent, the residue was precipitation with methanol to give 22.0 g compound 147 as light yellow solid.

5-Bromouridine is a uridine (U829910) derivative and is often incorporated into RNA in order to detect immunocytochemically and analyzed by cytometry.

Molecular Weight:323.10
XLogP3:-1.1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:321.98005
Monoisotopic Mass:321.98005
Topological Polar Surface Area:119
Heavy Atom Count:18
Complexity:414
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes