Methanesulfonic Acid → HCID 24904076, compound

HRID 1195434Notes

Reaction equation

HRID 1195434 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:18]S(O)(=O)=O>C(OCC)(OCC)OCC>[Cl:8][C:5]1[N:4]=[C:3]2[C:2]([N:1]=[CH:18][N:9]2[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 53742305HCID 53742305, compound

Product 1

HCID 24904076HCID 24904076, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

6.5 g (25.7 mmol) of 5-amino-2-chloro-4-[N-(2-fluorobenzyl)-amino]-pyrimidine are dissolved at room temperature in 65 ml of triethyl orthoformate. 30 mg of methanesulfonic acid are added to the solution and the reaction mixture is then stirred for 15 hours at room temperature. The reaction mixture is then concentrated by evaporation and the residue is chromatographed on silica gel with toluene/ethyl acetate (3:1) as eluant. The eluate is concentrated by evaporation and the residue obtained is recrystallised from dichloromethane/diethyl ether. In this manner 2-chloro-9-(2-fluorobenzyl)-9H-purine is obtained in the form of colourless crystals having a melting range of from 103° to 104°.

Workup

  1. concentrationThe reaction mixture is then concentrated by evaporation
  2. customthe residue is chromatographed on silica gel with toluene/ethyl acetate (3:1) as eluant
  3. concentrationThe eluate is concentrated by evaporation
  4. customthe residue obtained
  5. customis recrystallised from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-62115ab0c7504e6ebd113538db6f267a
Source dataset
uspto-grants-1992_05
Patent number
US05110818

Reaction notes

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