Reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[C:6]([S:12][CH3:13])[N:7]=[N:8][C:9]=1[CH:10]=O)[CH3:2].CO[C:16]1[CH:17]=[C:18]([CH2:24][C:25]#[N:26])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+]>C1COCC1>[CH3:23][O:22][C:20]1[CH:19]=[C:18]([C:24]2[C:25](=[NH:26])[N:3]([CH2:1][CH3:2])[C:4]3[N:5]=[C:6]([S:12][CH3:13])[N:7]=[N:8][C:9]=3[CH:10]=2)[CH:17]=[C:16]([O:30][CH3:27])[CH:21]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 5.0 g (25.2 mmol) of 5-ethylamino-3-methylsulfanyl-1,2,4-triazine-6-carbaldehyde in 125 mL of THF was added 6.7 g (37.8 mmol) of 3,5-dimethoxyphenylacetonitrile followed by 17.4 g (126.1 mmol) of potassium carbonate. The reaction mixture was warmed at 65° C. for 2 days, concentrated under vacuum, diluted with ethyl acetate, and washed three times with a saturated solution of sodium bicarbonate, once with water and brine. The organic phase was dried over magnesium sulfate, filtered, decolorized with charcoal, filtered through celite, and concentrated to give a dark orange oil. The crude oil was chromatographed through silica eluted with 2:2:6 to 2:3:5 dichloromethane/ethyl acetate/hexane to give 5.4 g (59%) of the title compound as a yellow amorphous solid. MS (APCI) (m+1)/z 358.1.
Workup
- concentrationconcentrated under vacuum
- additiondiluted with ethyl acetate
- washwashed three times with a saturated solution of sodium bicarbonate
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- filtrationfiltered through celite
- concentrationconcentrated
- customto give a dark orange oil
- customThe crude oil was chromatographed through silica
- washeluted with 2:2:6 to 2:3:5 dichloromethane/ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-1ff6d4ea9ad244b79484e60cc61fffa5
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06683183B2
Linked notes
Loading…