2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-{[(5-Bromopyridin-3-yl)imino]methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 598003

Reaction equation

[CH:1](OCC)(OCC)OCC.[CH3:11][C:12]1([CH3:20])[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[O:13]1.[NH2:21][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([Br:28])[CH:27]=1>C(O)C>[Br:28][C:26]1[CH:27]=[C:22]([N:21]=[CH:1][CH:15]2[C:16](=[O:18])[O:17][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:19])[CH:23]=[N:24][CH:25]=1

Participants

Conditions

Temperature: 92 °C

Procedure

A mixture of triethyl orthoformate (10 mL, 60.1 mmol) and 2,2-dimethyl-[1,3]-dioxane-4,6-dione (40.9 g, 0.23 mol)(Meldrum's acid) was heated at 92° C. for 90 minutes and then cooled to 70° C. over one hour. 3-Amino-5-bromopyridine (40.9 g, 0.20 mol) was slowly added over 10 minutes with an ethanol rinse while maintaining the reaction temperature between 60 and 70° C. The reaction was then heated for an additional 20 minutes and allowed to cool to room temperature. The reaction mixture was filtered and washed with ethanol (150 mL) yielding a tan solid. The solid was dried under vacuum for 2 hours to yield 59.14 g of 5-{[(5-bromopyridin-3-yl)imino]methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione as a light yellow crystalline solid, mp 200-202° C.

Workup

temperaturecooled to 70° C. over one hour
washrinse
temperaturewhile maintaining the reaction temperature between 60 and 70° C
temperatureThe reaction was then heated for an additional 20 minutes
temperatureto cool to room temperature
filtrationThe reaction mixture was filtered
washwashed with ethanol (150 mL)
customyielding a tan solid
customThe solid was dried under vacuum for 2 hours

Sources & evidence

ORD record: ord-f564f970fd1a432a8691f6658f8da53e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897609B2

Linked notes

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