Potassium Carbonate → 4-chloro-1-methyl-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-1H-pyrazolo[3,4-d]pyrimidine
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[OH:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[C:31]2[C:26](=[N:27][CH:28]=[N:29][C:30]=2[Cl:32])[N:25]([CH3:33])[N:24]=1>>[Cl:32][C:30]1[N:29]=[CH:28][N:27]=[C:26]2[N:25]([CH3:33])[N:24]=[C:23]([CH2:22][O:14][C:3]3[CH:4]=[C:5]([C:8]4[O:9][C:10]([CH3:13])=[N:11][N:12]=4)[CH:6]=[CH:7][C:2]=3[CH3:1])[C:31]=12Participants
Reactant 3
Product 1
Procedure
A mixture of 2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol (73.3 mg, 0.385 mmol) and potassium carbonate (60.9 mg, 0.432 mmole) was stirred at room temperature for 30 minutes before 3-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (89.6 mg, 0.343 mmole, Example 5) was added. The reaction was stirred at room temperature overnight and then concentrated under reduced pressure to remove dimethylformamide. The residue was dissolved in ethyl acetate, washed with water, dried and concentrated. The crude product was either used directly in the next step or purified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40) to give pure 4-chloro-1-methyl-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-1H-pyrazolo[3,4-d]pyrimidine as a white solid. (Yield 34.9 mg).
Workup
- additionwas added
- concentrationconcentrated under reduced pressure
- customto remove dimethylformamide
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with water
- customdried
- concentrationconcentrated
- custompurified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40)
Sources & evidence
- ORD record
- ord-cb2b7bcc4f1945f9ba4aa3ae14126f4b
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968554B2
Reaction notes
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