4-Fluorobenzyl chloride → 6-Amino-2-chloro-9-(4-fluorobenzyl)purine

HRID 2269146Notes

Reaction equation

HRID 2269146 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:23][C:22]1[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 949042-Chloroadenine

Product 1

HCID 115146366-Amino-2-chloro-9-(4-fluorobenzyl)purineYield 1,970.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Amino-2-chloropurine (5.02 g) and potassium carbonate (5 g, 36 mmol) were suspended in DMF (200 ml) and thereto was added 4-fluorobenzyl chloride (5 ml, 42 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo to dryness, and to the residue was added water. The mixture was extracted with chloroform and the organic layer was washed with water, dried on sodium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (162 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. additionto the residue was added water
  3. extractionThe mixture was extracted with chloroform
  4. washthe organic layer was washed with water
  5. customdried on sodium sulfate
  6. concentrationconcentrated in vacuo to dryness
  7. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-de60888fa9cc4327bb7238ebcbcc63fe
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

Loading…