Methylamine → HCID 54401962, compound
Reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:4]([N:19]([CH3:21])[CH3:20])[N:3]=1.[CH3:22][NH2:23]>>[CH3:20][N:19]([C:4]1[N:3]=[C:2]([NH:23][CH3:22])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[CH3:21]Participants
Procedure
2.5 g (8.2 mmol) of 2-chloro-6-(N,N-dimethylamino)-9-(2-fluorobenzyl)-9H-purine (Example 1) and 10 ml of ethanolic N-methylamine solution (16%) are heated for 120 hours at 80° to 85° in an autoclave. The reaction mixture is then concentrated by evaporation under reduced pressure. The residue is taken up in dichloromethane. The dichloromethane phase is washed twice with water, dried over magnesium sulfate and concentrated by evaporation. the residue is chromatographed on silica gel with toluene/ethyl acetate (10:1) as eluant. The eluate is concentrated by evaporation and the residue obtained is recrystallised from dichloromethane/hexane. In this manner 6-(N,N-dimethylamino)-9-(2-fluorobenzyl)2-(N-methylamino)-9H-purine is obtained in the form of colourless needles having a melting point of 100°.
Workup
- concentrationThe reaction mixture is then concentrated by evaporation under reduced pressure
- washThe dichloromethane phase is washed twice with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated by evaporation
- customthe residue is chromatographed on silica gel with toluene/ethyl acetate (10:1) as eluant
- concentrationThe eluate is concentrated by evaporation
- customthe residue obtained
- customis recrystallised from dichloromethane/hexane
Sources & evidence
- ORD record
- ord-662642f50cbf4f3ca45753900796ea8e
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05110818
Reaction notes
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