Potassium Carbonate → 8-bromo-7-(2-chloro-6-fluorobenzyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
Reaction equation
[Br:1][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:23]=1[CH2:24]Br.[K]>O.CS(C)=O.C(O)C>[Br:1][C:2]1[N:11]([CH2:24][C:23]2[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:22]=2[Cl:21])[C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A solution of 8-bromotheophylline (10 g, 39 mmol) in 30 mL water was treated with potassium carbonate (2.6 g, 48 mmol). The reaction mixture was refluxed until dissolved. Ethanol (30 mL) was added to the hot reaction mixture and the resulting potassium salt was filtered, washed with acetone, and dried in a 100° C. vacuum oven. A solution of 2-chloro-6-fluorobenzyl bromide (5.3 g, 24 mmol) in 10 mL DMSO was treated with the solid potassium salt The reaction mixture was heated to 100° C. for 1 hour and cooled. Upon addition of 5 mL water, the mixture was collected by filtration and dried in a vacuum oven to yield a white solid (6.0 g, 89% yield): 1H NMR (CDCl3, 300 MHz) 7.37-7.21 (m, 2H), 7.07-6.96 (m, 1H), 5.87 (s, 2H), 3.60 (s, 3H), 3.42 (s, 3H); MS (ESP+) m/e 402 (MH+).
Workup
- temperatureThe reaction mixture was refluxed
- dissolutionuntil dissolved
- filtrationthe resulting potassium salt was filtered
- washwashed with acetone
- customdried in a 100° C. vacuum oven
- temperaturecooled
- filtrationthe mixture was collected by filtration
- customdried in a vacuum oven
Sources & evidence
- ORD record
- ord-e5679d5a013c4af3a4c01a9eec0b48db
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495004B2
Reaction notes
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