Pyridine → (8-Benzenesulphonyl-2-methyl-7-methylsulphanyl-pyrazolo[1,5-a][1,3,5]triazin-4-yl)-methylamine
Reaction equation
[C:1]1([S:7]([C:10]2[C:11]([S:21][CH3:22])=[N:12][N:13]3[C:18](=O)[NH:17][C:16]([CH3:20])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:23]1C=CC=C[CH:24]=1>O=P(Cl)(Cl)Cl>[C:1]1([S:7]([C:10]2[C:11]([S:21][CH3:22])=[N:12][N:13]3[C:18]([NH:23][CH3:24])=[N:17][C:16]([CH3:20])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A suspension of 0.36 g (1 mmol) of 8-benzenesulphonyl-2-methyl-7-methylsulphanyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one in 20 ml of POCl3 was treated with 0.12 ml (1.5 mmol) of pyridine and heated 110° C. for 3 hrs. The reaction solution was cooled to RT and evaporated. The residue was dried azeotropically twice with 50 ml of toluene each time. The thus-obtained residue was taken in 10 ml of 2N methylamine in tetrahydrofuran and stirred at room temperature for 4 hrs. The reaction solution was evaporated and partitioned between H2O and AcOEt. The organic phase was washed with H2O and sat. NaCl solution, dried (MgSO4), filtered and evaporated. Chromatography (SiO2, AcOEt/hexane 1:1) yielded 0.28 g (80%) of (8-benzenesulphonyl-2-methyl-7-methylsulphanyl-pyrazolo[1,5-a][1,3,5]triazin-4-yl)-methylamine as white crystals, m.p. 285° (dec).
Workup
- temperatureThe reaction solution was cooled to RT
- customevaporated
- dry with materialThe residue was dried azeotropically twice with 50 ml of toluene each time
- customThe reaction solution was evaporated
- custompartitioned between H2O and AcOEt
- washThe organic phase was washed with H2O and sat. NaCl solution
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-9921df9e12f9427098bb7ae60516bb07
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06194410B1
Reaction notes
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