2,2-Dimethyl-1,3-dioxane-4,6-dione → 1,3-Dioxane-4,6-dione, 5-[[(6-methoxy-3-pyridinyl)amino]methylene]-2,2-dimethyl-

HRID 2274957Notes

Reaction equation

HRID 2274957 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:10][C:11]1([CH3:19])[O:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[O:12]1.[CH2:20](OC(OCC)OCC)C>C(O)C>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][CH:20]=[C:14]2[C:15](=[O:17])[O:16][C:11]([CH3:19])([CH3:10])[O:12][C:13]2=[O:18])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 42557991,3-Dioxane-4,6-dione, 5-[[(6-methoxy-3-pyridinyl)amino]methylene]-2,2-dimethyl-Yield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A double jacketed flask was charged with 5-amino-2-methoxypyridine (500 g, 1 eq.), 2,2-dimethyl-1,3-dioxane-4,6-dione (697 g, 1.2 eq.), triethylorthoformate (740 mL, 1.1 eq.) and ethanol (4 L). The mixture was heated to reflux for one hour. The dark suspension obtained was cooled to 5° C. and the mixture was filtered. The product was washed with ethanol (1 L) and dried on a rotary evaporator to obtain a purple solid (1058 g; 95% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. customThe dark suspension obtained
  4. filtrationthe mixture was filtered
  5. washThe product was washed with ethanol (1 L)
  6. customdried on a rotary evaporator
  7. customto obtain a purple solid (1058 g; 95% yield)

Sources & evidence

ORD record
ord-c9fa70524b2c448794df89a2323cec1c
Source dataset
uspto-grants-2015_09
Patent number
US09127002B2

Reaction notes

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