4-Amino-2,6-dichloropyridine → HCID 178516428, compound

HRID 1473501Notes

Reaction equation

HRID 1473501 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C[O:11][CH:12]=[C:13]1C(=O)OC(C)(C)O[C:14]1=O>CC(O)C>[Cl:9][C:4]1[N:3]=[C:2]([Cl:1])[CH:7]=[C:6]2[C:5]=1[C:12]([OH:11])=[CH:13][CH:14]=[N:8]2

Participants

4

Reactant 2

HCID 1376524-Amino-2,6-dichloropyridineHCID 1521115-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 178516428HCID 178516428, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a flask equipped with a reflux condenser, 2,6-dichloropyridin-4-amine (2.00 g, 12.27 mmol) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.398 g, 12.88 mmol) were dissolved in IPA (12.00 mL) and heated to 100° C. for 1 hour. The reaction was cooled to room temperature and the solids were filtered. The solids were added to a microwave vial followed by dichlorobenzene (12.00 mL). The vial was capped and heated to 250° C. for 15 minutes. The reaction was purified via silica gel MPLC chromatography (40 g), eluting with 0 to 100% ethyl acetate in heptanes. The fractions were collected and the solvent was removed under reduced pressure to provide 1.63 g of 5,7-dichloro-1,6-naphthyridin-4-ol as an off white solid. m/z (ESI) 215.1 (M+H)+.

Workup

  1. customTo a flask equipped with a reflux condenser
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe solids were filtered
  4. additionThe solids were added to a microwave
  5. customThe vial was capped
  6. temperatureheated to 250° C. for 15 minutes
  7. customThe reaction was purified via silica gel MPLC chromatography (40 g)
  8. washeluting with 0 to 100% ethyl acetate in heptanes
  9. customThe fractions were collected
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-25b8a22242e544d490468aae6e688d76
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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