Diisopropylethylamine → 6-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridazine-4-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
The title compound from Example 18.4 (0.90 g, 5.35 mmol) was stirred in dimethylformamide (20 mL) and diisopropyl ethylamine (1.39 mL, 8.025 mmol) at 0° C. and (2-chloromethoxy-ethyl)-trimethyl-silane (1.88 mL, 10.70 mmol) was added and the reaction was allowed to continue to stir at 0° C. for 2 hours and then overnight at r.t. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated onto silica gel. The product was purified by column chromatography (0-20% EtOAc/hexanes) to afford the title compound as a clear oil (0.85 g, 53%).
Workup
- customovernight
- customat r.t
- washwashed with water and brine
- dry with materialThe organic phase was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated onto silica gel
- customThe product was purified by column chromatography (0-20% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-56de719ec7044f52a82a8837ab42c978
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772235B2
Reaction notes
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