Potassium Carbonate → 9-(2-Chloro-6-fluorobenzyl)-6-methylaminopurine

HRID 905325Notes

Reaction equation

HRID 905325 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67955N6-MethyladenineHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzene

Product 1

HCID 1298019-(2-Chloro-6-fluorobenzyl)-6-methylaminopurineYield 63%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 6-methylaminopurine (7.45 g, 50 mmols), potassium carbonate (6.9 g, 50 mmols) and N,N-dimethylacetamide (250 ml) was added 2-chloro-6-fluorobenzyl chloride (17.9 g, 100 mmols), 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-(2-chloro-6-fluorobenzyl)-6-methylaminopurine as colorless needles (9.08 g, yield 63%), m.p. 188°-190° C.

Workup

  1. customto react at 110° C. for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customto remove insoluble materials
  5. concentrationthe filtrate was concentrated to dryness under reduced pressure
  6. additionUpon addition of water to the resultant residue
  7. filtrationthe formed precipitate was collected by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b16b0f42b13f435b9b6ac486943281c4
Source dataset
uspto-grants-1983_12
Patent number
US04423219

Reaction notes

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