4-Aminopyridine → HCID 9953049, compound

HRID 1841446Notes

Reaction equation

HRID 1841446 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:22](=[O:23])[N:21]([CH2:24][CH3:25])[C:14]3[N:15]=[C:16](SC)[N:17]=[N:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:22](=[O:23])[N:21]([CH2:24][CH3:25])[C:14]3[N:15]=[C:16]([NH:26][C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)[N:17]=[N:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

3

Reactant 2

HCID 17274-Aminopyridine2×HCID 12098505HCID 12098505, compound

Product 1

HCID 9953049HCID 9953049, compoundYield 30.2%

Procedure

A homogenious mixture of 1.8 g (5.0 mmol) of 7-(3,5-dimethoxy-phenyl)-5-ethyl-3-methylsulfanyl-5H-pyrido[2,3-e]-1,2,4-triazin-6-one and 3.3 g (35.2 mmol) of 4-aminopyridine was heated at 150° C. for 2 days in a sealed reaction vessel, during which time the sublimed 4-aminopyrdine was reintroduced to the reaction mixture. At the end of 2 days, the sublimed 4-aminopyridine was removed, and the remaining mixture was triturated under 1:9 methanol/chloroform at room temperature and filtered. The solid was suspended in 60 mL of hot chloroform while methanol was added to produce a near homogeneous solution that was filtered and set aside for 6 days. The crystals were collected, washed with chloroform, and dried under house vacuum to give 610 mg (30%) of the title compound as yellow platelets. Mp=316-318° C. (dec).

Workup

  1. additionwas reintroduced to the reaction mixture
  2. customAt the end of 2 days, the sublimed 4-aminopyridine was removed
  3. customthe remaining mixture was triturated under 1:9 methanol/chloroform at room temperature
  4. filtrationfiltered
  5. additionwas added
  6. customto produce a near homogeneous solution that
  7. filtrationwas filtered
  8. customThe crystals were collected
  9. washwashed with chloroform
  10. customdried under house vacuum

Sources & evidence

ORD record
ord-9ae1315af2b547319560bdbdb0d69eb8
Source dataset
uspto-grants-2004_01
Patent number
US06683183B2

Reaction notes

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