Water → 2-[6-(Ethylsulfanyl)pyrimidin-4-yl]-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one
Reaction equation
Cl.Cl[C:3]1[N:8]=[CH:7][N:6]=[C:5]([N:9]2[C:13](=[O:14])[C:12]([N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)=[CH:11][NH:10]2)[CH:4]=1.[CH2:20]([SH:22])[CH3:21].[H-].[Na+].O>CN(C=O)C>[CH2:20]([S:22][C:3]1[N:8]=[CH:7][N:6]=[C:5]([N:9]2[C:13](=[O:14])[C:12]([N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)=[CH:11][NH:10]2)[CH:4]=1)[CH3:21]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
200 mg (0.7 mmol) of the compound from Example 52A are suspended in 1.1 ml DMF under argon. 61 mg (1.0 mmol) ethanethiol are added. 35 mg (0.8 mmol, 60% strength in mineral oil) sodium hydride are added cautiously, while cooling with ice. The mixture is stirred at RT for 2.5 h. 1 ml water is subsequently added dropwise and the mixture is subsequently stirred at RT for 15 min. The clear reaction solution obtained is purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product-containing fractions are combined, the mixture is concentrated and the residue is dried under a high vacuum.
Workup
- temperaturewhile cooling with ice
- stirringthe mixture is subsequently stirred at RT for 15 min
- customThe clear reaction solution obtained
- customis purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)
- concentrationthe mixture is concentrated
- customthe residue is dried under a high vacuum
Sources & evidence
- ORD record
- ord-e27112b3c7b143bc9717464d18944d19
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09168249B2
Reaction notes
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