4-Aminopyridine → HCID 59427333, compound

HRID 1013705Notes

Reaction equation

HRID 1013705 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[CH:11](OCC)(OCC)OCC.[N:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1>CCCCCC>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[C:5](=[CH:11][NH:27][C:24]2[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=2)[C:4](=[O:9])[O:3]1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformate

Product 1

HCID 59427333HCID 59427333, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

In a dried 2-necked RBF equipped with reflux condenser and inert atmosphere, 2,2-dimethyl-1,3-dioxane-4,6-dione (2.33 g, 16 mmol) was dissolved in triethyl orthoformate (16 ml, 97 mmol) and the mixture was stirred at 100° C. under nitrogen for 1.5 h. On complete consumption of starting material (tic), pyridin-4-amine (1.5 g, 16 mmol) was added and heating continued for 4.5 h. The reaction mixture was cooled down to RT and poured into hexane (50 mL). The solid was filtered off and washed with hexane to afford 2,2-dimethyl-5-((pyridin-4-ylamino)methylene)-1,3-dioxane-4,6-dione as an orange solid.

Workup

  1. customIn a dried 2-necked RBF equipped
  2. temperaturewith reflux condenser
  3. additionwas added
  4. temperatureheating
  5. waitcontinued for 4.5 h
  6. temperatureThe reaction mixture was cooled down to RT
  7. filtrationThe solid was filtered off
  8. washwashed with hexane

Sources & evidence

ORD record
ord-108d9963829949a7a3e528f877daf3c9
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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