Potassium Carbonate → 3-(5-benzyloxy-2-methyl-phenoxymethyl)-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:16])=[C:13]([OH:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[N:31][C:32]=2[Cl:34])[N:27]([CH3:35])[N:26]=1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:16])=[C:13]([CH:14]=1)[O:15][CH2:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[N:31][C:32]=2[Cl:34])[N:27]([CH3:35])[N:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
A mixture of 5-benzyloxy-2-methyl-phenol (83.4 mg, 0.389 mmol, 37009-93A) and potassium carbonate (61.8 mg, 0.438 mmole) was stirred at room temperature for 30 minutes before 3-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (89.8 mg, 0.344 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 3-(5-benzyloxy-2-methyl-phenoxymethyl)-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine as a white solid. (Yield 48.0 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-bd8e1781ab47451e855e072bdc21591c
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968554B2
Reaction notes
Loading…