ChemicalBook CAS DataBase List 7,8-Dimethyl-10-carboxymethylisoalloxazine

7,8-Dimethyl-10-carboxymethylisoalloxazine synthesis

9synthesis methods

Product Name:7,8-Dimethyl-10-carboxymethylisoalloxazine
CAS Number:21079-31-2
Molecular formula:C14H12N4O4
Molecular Weight:300.27

7,8-dimethyl-10-formylmethylisoalloxazine

4250-90-2
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7,8-Dimethyl-10-carboxymethylisoalloxazine

21079-31-2
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Yield:21079-31-2 68%

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate;water in 1-methylcyclohex-1-ene;acetonitrile;tert-butyl alcohol at 0; for 2.08333 h;

Steps:

26.1

Step 1 Preparation of (7,8-Dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g1pteridin-10- yl)-acetic acid[0172] To a suspension of (7, 8-dimethyl-2, 4-dioxo-3, 4-dihydro-2H- benzo[g]pteridin-10-yl)- acetaldehyde (prepared by the method of Example 14) (50 mg, 0.18 mmol) in acetonitrile (2 ml), tert-butanol (8 mL), and methyl- 1-cyclohexene (3 mL) at 0 °C, a solution of sodium chlorite (122 mg, 1.35 mmol) and sodium dihydrogen phosphate (148 mg, 1.23 mmol) in water (2 mL) is added dropwise over 5 min. After 2 h, the reaction mixture is diluted with water and the organic layer is discarded. The aqueous phase is concentrated under vacuum and the resultant crude mixture is purified via preparative HPLC. (7,8-Dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)- acetic acid (36 mg) is isolated following lyophilization of the appropriate fractions (yield: 68%). LC-MS m/z 301.1 [M+H], retention time = 1.68 min.

References:

WO2010/19208,2010,A1 Location in patent:Page/Page column 202-203

83-88-5 Synthesis