Iodine chloride → 1-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-iodouracil
Reaction equation
[I:1]Cl.[OH:3][CH2:4][CH:5]([CH2:16][OH:17])[CH2:6][CH2:7][N:8]1[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]1=[O:10]>CO>[OH:3][CH2:4][CH:5]([CH2:16][OH:17])[CH2:6][CH2:7][N:8]1[CH:15]=[C:14]([I:1])[C:12](=[O:13])[NH:11][C:9]1=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Iodine monochloride (500 mg, 3.08 mmol) was added to a solution of 18 (360 mg, 1.68 mmol) in dry methanol (25 ml) and the reaction mixture was stirred at 50° C. for 90 min. and then the methanol was removed in vacuo. The dry residue was treated with 5.0 ml of conc. ammonium hydroxide in 25 ml of methanol with stirring at 50° C. for 1 h. The crude reaction mixture was purified by elution from a column of silica gel by using dichloromethane-methanol (92:8, v/v) as eluent. The product 19 was obtained in 59.2% yield as a colorless gum.
Workup
- customthe methanol was removed in vacuo
- additionThe dry residue was treated with 5.0 ml of conc. ammonium hydroxide in 25 ml of methanol
- stirringwith stirring at 50° C. for 1 h
- customThe crude reaction mixture
- customwas purified by elution from a column of silica gel
Sources & evidence
- ORD record
- ord-6242d3b467be497f8970d67536aca8cf
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08227594B2
Reaction notes
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