Tetrahydrofuran → 6'-[6-(methylthio)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

HRID 2191903Notes

Reaction equation

HRID 2191903 reaction equation
C([O-])=O.[NH4+].O1CCCC1.C([N:13]1[C:21](=[O:22])[C:20]2[C:15](=[N:16][C:17]([S:23][CH3:24])=[N:18][CH:19]=2)[N:14]1[C:25]1[N:30]=[C:29]([N:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]2=[O:37])[CH:28]=[CH:27][CH:26]=1)C=C>C(Cl)(Cl)Cl>[CH3:24][S:23][C:17]1[N:16]=[C:15]2[N:14]([C:25]3[N:30]=[C:29]([N:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]4=[O:37])[CH:28]=[CH:27][CH:26]=3)[NH:13][C:21](=[O:22])[C:20]2=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 684275366'-[2-allyl-6-(methylthio)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

Product 1

HCID 684275866'-[6-(methylthio)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ammonium formate (964 mg) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II)/dichloromethane complex (208 mg) were added to a tetrahydrofuran (10 mL) solution of 6′-[2-allyl-6-(methylthio)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2′-bipyridin-2-one (1 g), and heated overnight under reflux. The reaction liquid was cooled to room temperature, then diluted with chloroform, and washed with water and saturated saline water in order. The organic layer was dried with anhydrous magnesium sulfate. The insoluble matter was dissolved, and then the solvent was evaporated away to give crude 6′-[6-(methylthio)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2′-bipyridin-2-one.

Workup

  1. temperatureheated overnight
  2. temperatureunder reflux
  3. customThe reaction liquid
  4. washwashed with water and saturated saline water in order
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. dissolutionThe insoluble matter was dissolved
  7. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-4090580e5efc44f5abfd3347e35eece3
Source dataset
uspto-grants-2012_12
Patent number
US08329711B2

Reaction notes

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