Trimethyl orthoformate → 5-[(3-Bromo-2-methoxy-pyridin-4-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 219145Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11](OC)(OC)OC.[NH2:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([O:25][CH3:26])[C:20]=1[Br:27]>CCCCCC>[Br:27][C:20]1[C:21]([O:25][CH3:26])=[N:22][CH:23]=[CH:24][C:19]=1[NH:18][CH:11]=[C:6]1[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

A two necked round bottomed flask equipped with a reflux condenser was charged with Meldrum's acid (15.6 g, 108 mmol) and trimethyl orthoformate (143 mL). The reaction mixture was heated 100° C. for 2 h. 4-amino-3-bromo-2-methoxypyridine (22 g, 108 mmol) was added and heating was continued for an additional 4 h at 100° C. The reaction mixture was allowed to cool to RT, diluted with hexane and filtered to obtain the product as a yellow solid.

Workup

customA two necked round bottomed flask equipped with a reflux condenser
temperatureheating
temperatureto cool to RT
filtrationfiltered

Sources & evidence

ORD record: ord-51e9526dbf1d4aabb40100df51e6b0c4
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198448B2

Reaction notes

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