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

HRID 40257Notes

Reaction equation

HRID 40257 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH3:11]OC(OC)OC.[NH2:18][C:19]1[CH:20]=[C:21]([O:25][CH3:26])[CH:22]=[N:23][CH:24]=1>CCCCCC>[CH3:26][O:25][C:21]1[CH:20]=[C:19]([NH:18][CH:11]=[C:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])[CH:24]=[N:23][CH:22]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 127035955-Methoxypyridin-3-ylamine

Product 1

HCID 673177565-[(5-Methoxy-pyridin-3-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
102.5 °C

Procedure

A two-necked round bottomed flask equipped with a reflux condenser was charged with Meldrum's acid (14.4 g, 100 mmol) and trimethylorthoformate (100 mL). The reaction mixture was heated at 100-105° C. for 2 h. 5-amino-3-methoxy pyridine (12.5 g, 100 mmol) was added to the reaction mixture and heating was continued for an additional 4 h at the same temperature. The reaction mixture was allowed to cool to RT, diluted with hexane and filtered to obtain the product as light yellow solid.

Workup

  1. customA two-necked round bottomed flask equipped with a reflux condenser
  2. temperatureheating
  3. temperatureto cool to RT
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a4ee22d2637b442a866f028382f7e6fd
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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