Vinyl Acetate → 1-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-vinyluracil
Reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:2]=1.[OH-].[Ca+2].[OH-].[OH:23][CH2:24][CH:25]([CH2:37][OH:38])[CH2:26][CH2:27][N:28]1[CH:35]=[C:34](I)[C:32](=[O:33])[NH:31][C:29]1=[O:30].C(OC=C)(=O)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[OH:23][CH2:24][CH:25]([CH2:37][OH:38])[CH2:26][CH2:27][N:28]1[CH:35]=[C:34]([CH:1]=[CH2:2])[C:32](=[O:33])[NH:31][C:29]1=[O:30]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
A mixture of palladium (II) acetate (79 mg, 0.35 mmol), triphenylphosphine (185 mg, 0.7 mmol) and triethylamine (5 ml), (dried over calcium hydroxide) in dry DMF (80 ml) was maintained at 70° C. with stirring until an intense red color appeared. Compound 19 (2.36 gm, 6.95 mmol) and vinyl acetate (30 ml, 330 mmol) were then added, and the reaction was allowed to proceed at 70° C. for 6 h with stirring. The solvent was removed in vacuo and the residue obtained was extracted with water (2×50 ml). The water layer was washed with dichloromethane, evaporated in vacuo, and the residue obtained was purified by elution from a silica gel column using ethyl acetate-methanol (95:5, v/v) as eluent to give 20 as a viscous oil (800 mg, 48%).
Workup
- stirringwith stirring
- customThe solvent was removed in vacuo
- customthe residue obtained
- extractionwas extracted with water (2×50 ml)
- washThe water layer was washed with dichloromethane
- customevaporated in vacuo
- customthe residue obtained
- customwas purified by elution from a silica gel column
Sources & evidence
- ORD record
- ord-bcadf2594cd346e8baa5b1374bea1ba2
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08227594B2
Reaction notes
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