5-Iodouridine

White powder

In a round bottom flask, uridine (1 g, 4.1 mmol) and iodine powder (1 .15 g, 4.5 mmol) were dissolved in a mixture of CHCIIodine (0.508 g) in 2.0 mL of methanol was added dropwise to a suspension of silver sulfate (0.624 g) and uridine (0.488 g) in 10 mL of methanol. The reaction mixture was stirred at room temperature until the orange color disappeared. The precipitate was removed by filtration. The filtrate was concentrated and recrystallized from methanol, affording a pale yellow solid (78percent). Take uridine (13.06g, 53.50mmol) was dissolved in 252ml of dilute nitric acid, heated to 110 , Was added (10.09g, 39.92mmol) elemental iodine, the reaction was monitored by thin layer chromatography case, exhibitionEluent, CH2Cl2: CH3OH = 7: 1, about 4 hours after the reaction raw material point disappears, and the reactionComplete, the reaction was stopped. After leaving to cool and extracted 3 times with 30ml petroleum ether, collecting the lower solution, Upper solution was extracted with 30ml of deionized water, lower solutions were twice extracted. Standing whiteThe solid precipitated, placed in the upper refrigerator overnight, a lot of white solid was obtained, that is, uridine 5-I-(14.30g, 38.64mmol), the yield was 72.22percentGeneral procedure: The suspension of nucleosides 2a, b (19 mmol) in water (5.7 mL) was treated with HIO3(9.7 mmol, 1.7 g), AcOH (15.2 mL) and a solution of iodine (11.22 mmol, 2.85 g) inCCl4 (3.8 mL). The resulting mixture was stirred at 40C for 2 h until the starting materialwas consumed or some by-product was formed (monitored by HPLC). After that, water (20 mL) was added. The reaction mixture was cooled to 4C and filtered. The precipitatewas washed with water (2 £ 10 mL). The combined solutions were diluted withwater (250 ml) and extracted with benzene (3 £ 150 mL). The aqueous layer was evaporatedunder reduced pressure. The product was purified by RPC in a linear gradient ofEtOH in water (0–30percent) to give the product 3a, b.Compound 8 (3.87 mmol, 1.92 g) was dissolved in MeOH (20 ml) and 28percent aq. NH3(20 mL) was added. The reaction was completed in 1 h at ambient temperature(monitored by TLC, CH2Cl2:MeOH, 9:1). The reaction mixture was evaporated and thenco-evaporated with a mixture of EtOH:EtOAc:toluene (1:1:2; 2 £ 80 mL). The crudeproduct was purified by silica gel column chromatography using CH2Cl2:MeOH (1:4) togive the 5-iodouridine 3a in 98percent yield (3.83 mmol, 1.42 g), as white solid.The synthetic mRNA construct of claim 1, wherein the mRNA construct comprises one or more chemically-modified nucleotides selected from the group of 5-hydroxyuridine, 5-methyluridine, 5, 6-dihydro-5-methyluridine, 2'-O-methyluridine, 2'-O-methyl-5-methyluridine, 2'-fluoro-2'-deoxyuridine, 2'-amino-2'-deoxyuridine, 2'-azido-2'-deoxyuridine, 4-thiouridine, 5-hydroxymethyluridine, 5-carboxyuridine, 5-carboxymethylesteruridine, 5-formyluridine, 5-methoxyuridine, 5-propynyluridine, 5-bromouridine,

Molecular Weight:370.10
XLogP3:-1.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:369.96618
Monoisotopic Mass:369.96618
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