Acetic Acid → 1-(4-Dimethylphosphonomethoxytetrahydro-2-furyl)thymine

HRID 2293719

Reaction equation

CO[CH:3]1[O:7][CH:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][CH2:4]1.CO[P:19]([O:23][CH3:24])([O:21][CH3:22])=[O:20].[C:25](O)(=[O:27])C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:24][O:23][P:19]([CH2:25][O:27][CH:4]1[CH2:3][O:7][CH:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5]1)([O:21][CH3:22])=[O:20]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-(5-methoxytetrahydro-2-furyl)thymine (5.2 g, 23 mmol) and dimethylphosphonomethanol (6.5 g, 44 mmol) in toluene was added acetic acid (5 mL) and p-toluenesulfonic acid monohydrate (500 mg, 2.6 mmol). The solution was heated at 100° C. for 2 hr and the resulting insoluble solid was removed by suction filtration. After removal of the solvent under reduced pressure, the residual oil was chromatographed on silica gel using CH2Cl2 /5% MeOH as eluent to give the title compound as a cis/trans mixture (6:4): yield 5.0 g (60%).

Workup

customthe resulting insoluble solid was removed by suction filtration
customAfter removal of the solvent under reduced pressure
customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record: ord-5d083594f26649d3af6216a68059bd2b
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686611

Linked notes

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