Ammonia → methyl 3-[2-allyl-6-(methylthio)-3-oxo-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl]benzoate
Reaction equation
N1C=CC=CC=1.[CH2:7]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=2)[NH:11]1)[CH:8]=[CH2:9].[CH3:22][O:23][C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)=[O:25].N>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O.C(Cl)(Cl)Cl>[CH2:7]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=2)[N:11]1[C:30]1[CH:31]=[C:26]([CH:27]=[CH:28][CH:29]=1)[C:24]([O:23][CH3:22])=[O:25])[CH:8]=[CH2:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
20 mL of pyridine was added to a chloroform solution of 7.5 g of 2-allyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 6.1 g of copper(II) acetate and 10 g of [3-(methoxycarbonyl)]phenylboronic acid, and stirred at room temperature for 3 days. Aqueous 30% ammonia solution and saturated saline water were added to the reaction liquid in that order, and extracted with chloroform. The organic layer was washed with saturated saline water, then dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 6.7 g of methyl 3-[2-allyl-6-(methylthio)-3-oxo-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl]benzoate as a yellow oily substance.
Workup
- extractionextracted with chloroform
- washThe organic layer was washed with saturated saline water
- dry with materialdried with anhydrous magnesium sulfate
- customthe solvent was evaporated away
- customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-b749d91ec3cb4cfabad6d2234e0f914b
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791125B2
Reaction notes
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