Ammonia → methyl 3-[2-allyl-6-(methylthio)-3-oxo-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl]benzoate

HRID 1172626Notes

Reaction equation

HRID 1172626 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

8

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 671714702-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

Product 1

HCID 67171015methyl 3-[2-allyl-6-(methylthio)-3-oxo-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-1-yl]benzoateYield 55.7%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

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

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away
  5. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e43459982a464ff299e7b078720c6624
Source dataset
uspto-grants-2010_11
Patent number
US07834019B2

Reaction notes

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