3-Fluoroaniline → 2-Chloro-6-(3-fluoro-phenyl-amino)-purine

HRID 1514340Notes

Reaction equation

HRID 1514340 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16]>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:13]([F:12])[CH:14]=2)[N:3]=1

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 53244122,6-Dichloropurine

Product 1

HCID 219883282-Chloro-6-(3-fluoro-phenyl-amino)-purine

Procedure

This compound was prepared in a similar manner as described in example 2, by reaction of 2,6-dichloropurine with 3-fluoroaniline. The reaction mixture was then evaporated on a rotary vacuum evaporator and the residue was partitioned between ethyl acetate and 0.5 M HCl. The organic layer was washed with water, dried with MgSO4, and evaporated to give a yellow solid (3.72 g). The crude product was purified by flash chromatography. Yield: 2.20 g yellow crystalline powder. TLC (chloroform-methanol; 85:15): homogenous. HPLC purity: 98+%

Workup

  1. customThis compound was prepared in a similar manner
  2. customThe reaction mixture was then evaporated on a rotary vacuum evaporator
  3. customthe residue was partitioned between ethyl acetate and 0.5 M HCl
  4. washThe organic layer was washed with water
  5. dry with materialdried with MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-f92efac617564918b71439c874fbcddf
Source dataset
uspto-grants-2012_07
Patent number
US08222260B2

Reaction notes

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