6-chloro-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one synthesis
- Product Name:6-chloro-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one
- CAS Number:1350925-20-0
- Molecular formula:C7H6ClN3O
- Molecular Weight:183.6
1350925-19-7
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Yield:1350925-20-0 68%
Reaction Conditions:
Stage #1: ethyl (2-amino-6-chloropyridin-3-yl)glycinatewith sodium hydride in 1,4-dioxane;mineral oil; for 2 h;Reflux;
Stage #2: with hydrogenchloride;water in 1,4-dioxane;mineral oil at 20; pH=8 - 9;
Steps:
E; 3.3c
To a solution of ethyl 2-(2-amino-6-chloropyridin-3-ylamino)acetate (E-25) (4.58 g, 20 mmol, 1.0 eq) in dry 1,4-dioxane (50 mL) was added sodium hydride (60% in mineral oil, 240 mg, 6mmol, 0.3 eq), the resulting mixture was stirred at reflux for 2 h then cooled to RT and neutralized with con. HC1 to adjust the pH value to 8- 9, concentrated in vacuo to remove most of solvent and then filtered, the filter cake was washed with water and ethyl acetate / petroleum ether (1 : 1) and dried to afford the desired product 6-chloro-l,2-dihydropyrido[2,3-b]pyrazin- 3(4H)-one (E-26) (2.5g , 68% yield) as a pale solid. :H NMR (300 MHz, DMSO-+.
References:
WO2011/149937,2011,A1 Location in patent:Page/Page column 41; 85
146015-42-1
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40851-95-4
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27048-04-0
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