5-[BIS(METHYLSULFANYL)METHYLENE]-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE synthesis
- Product Name:5-[BIS(METHYLSULFANYL)METHYLENE]-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE
- CAS Number:100981-05-3
- Molecular formula:C9H12O4S2
- Molecular Weight:248.32
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Yield: 28.8%
Reaction Conditions:
Stage #1:cycl-isopropylidene malonate with carbon disulfide;triethylamine in dimethyl sulfoxide at 20; for 1 h;
Stage #2:methyl iodide in dimethyl sulfoxide at 0 - 20; for 15 h;
Steps:
16
Example 16;: 3-Amino-6- [4- (2-hydroxy-2-pyridin-2-yl-ethylamino)-piperidin-1-yl]-4- (2,2, 2-trifluoro-ethoxy) -thieno [2, 3-b] pyridine-2-carboxylic acid amide NNH, O 1) CS2, TEA 0 s S Sz Brt 2 2) Mel ps NaOEt i N NaH DMSO o o EtOH H THF H g i O,. i iN S NHZ S NHZ NaH, TfzNPh o I o Oxone ° < NH2 H O Fi O N S NH2 MeOH : H2 F Op N S O O F N N F F F MEOH N F F F H AcOH, H20 Na nu zu N 2- Po FF n F FF t NH2 N9NH2 N ° NH2 OH I % NH2 N N S 0 N S 0 ozon OH H 16 To a solution of 2, 2-dimethyl-1, 3-dioxane-4,6-dione (60.0 g, 416 mmol) in DMSO (150 mL) was added carbon disulfide (25 mL, 420 mmol) and triethylamine (116 mL, 832 mmol). The mixture was stirred at room temperature for lh then cooled to 0 °C and 52 mL (830 mmol) of iodomethane was added. The reaction mixture was allowed to slowly warm to room temperature and stirred for 15h. The mixture was decanted into an ice-H20 mixture and a solid was precipitated by agitation of the solution. The solid was collected by filtration, washed with a 1: 1 mixture of petroleum ether: Et2O, and dried under vacuum to provide 29.7 g (28.8%) of 5- (bis-methylsulfanyl-methylene)-2, 2-dimethyl- [1, 3] dioxane-4,6-dione as an orange solid.
References:
BOEHRINGER INGELHEIM PHARMACEUTICALS, INC. WO2005/56562, 2005, A1 Location in patent:Page/Page column 79
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342 suppliers
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100981-05-3
32 suppliers
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