Continuously updated synthesis method about 15568-85-1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15568-85-1, its application will become more common.

Some common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C8H10O5, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

4-Chloro-l,7-naphthyridine was prepared as follows (the compound may also be prepared according to the procedure on page 962 in Science of Synthesis, 2005, ,15., 947-985):; – Diisopropylethylamine (58.2 ml) was added to a stirred suspension of 3-aminopyridine- iV-oxide hydrochloride salt (49 g) and 5-(methoxymethylidene)-2,2-dimethyl-l,3-dioxane- 4,6-dione (62.2 g) in isopropanol (150 ml) and the resultant mixture was heated to 9O0C for 20 minutes. The mixture was cooled in an ice bath and the precipitate was isolated and washed in turn with cool isopropanol and diethyl ether and dried under vacuum at 50C. There was thus obtained 2,2-dimethyl-5-[(l -oxidopyridin-3-ylamino)methylidene]-l ,3-dioxane-4,6-dione (81.9 g; 1H NMR Spectrum: (DMSOd6) 1.68 (s, 6H)5 7.44 (m, IH), 7.61 (d, IH), 8.1 (d, IH), 8.52 (2s, IH), 8.66 (s, IH), 11.15 (br s, IH); Mass Spectrum: M-H” 263.; The 4-chloro-l,5-naphthyridine was prepared as follows :; -Diisopropylethylamine (58.2 ml) was added to a stirred suspension of 3-aminopyridine- iV-oxide hydrochloride salt (49 g) and 5-(methoxymethylidene)-2,2-dimethyl-l,3-dioxane- 4,6-dione (62.2 g) in isopropanol (150 ml) and the resultant mixture was heated to 9O0C for 20 minutes. The mixture was cooled in an ice bath and the precipitate was isolated and washed in turn with cool isopropanol and diethyl ether and dried under vacuum at 500C. There was thus obtained 2,2-dimethyl-5-[(l-oxidopyridin-3-ylamino)methylidene]-l,3-dioxane-4,6-dione (81.9 g; 1H NMR SPeCtTUm: (DMSOd6) 1.68 (s, 6H), 7.44 (m, IH), 7.61 (d, IH), 8.1 (d, IH), 8.52 (2s, IH), 8.66 (s, IH), 11.15 (br s, IH); Mass Spectrum: M-H” 263.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15568-85-1, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); A1;,
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