Potassium Carbonate → 9-(2-Chloro-6-fluorobenzyl)-6-methylaminopurine
Reaction equation
[CH3:1][NH:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH2:21]Cl>CN(C)C(=O)C>[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH2:21][N:7]1[CH:6]=[N:5][C:4]2[C:8]1=[N:9][CH:10]=[N:11][C:3]=2[NH:2][CH3:1]Participants
Procedure
To a mixture of 7.45 g of 6-methylaminopurine, 6.9 g of potassium carbonate and 250 ml of N,N-dimethylacetamide was added 17.9 g of 2-chloro-6-fluorobenzyl chloride, and the resultant mixture was allowed to react at 110° C. for 6 hours with stirring. After cooling, the reaction mixture was filtered to remove insoluble materials and the filtrate was concentrated to dryness under reduced pressure. Upon addition of water to the resultant residue, the formed precipitate was collected by filtration and recrystallized from ethanol to give 9.08 g of 9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine as colorless needles (yield: 63%), m.p. 188°-190° C. Nuclear magnetic resonance (NMR) spectrum of this product is identical with that of the corresponding compound synthesized in Example 1.
Workup
- customto react at 110° C. for 6 hours
- temperatureAfter cooling
- filtrationthe reaction mixture was filtered
- customto remove insoluble materials
- concentrationthe filtrate was concentrated to dryness under reduced pressure
- additionUpon addition of water to the resultant residue
- filtrationthe formed precipitate was collected by filtration
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-c605836847a64024b165ecd66fba807a
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04189485
Reaction notes
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