Ammonia → 2-allyl-6-(methylthio)-1-pyridin-2-yl-3H-pyrazolo[3,4-d]pyrimidin-3-one
Reaction equation
CNCCNC.[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].I[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+].N>[Cu]I.O1CCOCC1>[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:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[CH:8]=[CH2:9]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
N,N′-dimethylethylenediamine (2.4 mL) was added to a 1,4-dioxane (50 mL) solution of 2-allyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (4.44 g), copper(I) iodide (3.80 g), 2-iodopyridine (5.33 g) and potassium carbonate (3.80 g), and stirred overnight at 95° C. The reaction liquid was cooled, then aqueous ammonia was added thereto and extracted with ethyl acetate, washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the residue was crystallized with ethyl acetate to give the entitled compound as a white solid (5.15 g).
Workup
- customThe reaction liquid
- temperaturewas cooled
- extractionextracted with ethyl acetate
- washwashed with saturated saline water
- dry with materialdried with anhydrous magnesium sulfate
- customThe solvent was evaporated away under reduced pressure
- customthe residue was crystallized with ethyl acetate
Sources & evidence
- ORD record
- ord-64a8bf3483fb44b5b52e83bd2774ec5a
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329711B2
Reaction notes
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