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
2.4 mL of N,N′-dimethylethylenediamine was added to 1,4-dioxane (50 mL) solution of 4.44 g of 2-allyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one, 3.80 g of copper(I) iodide, 5.33 g of 2-iodopyridine and 3.80 g of potassium carbonate, and stirred overnight at 95° C. The reaction liquid was cooled, 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 crystallized with ethyl acetate to obtain 5.15 g of the entitled compound as a white solid.
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
- customcrystallized with ethyl acetate
Sources & evidence
- ORD record
- ord-024f61aeba4a4ad19bd0518f50f528fc
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198281B2
Reaction notes
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