1,4-Dioxane → HCID 178508856, compound

HRID 1588477Notes

Reaction equation

HRID 1588477 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](N)[C:5]2[CH:11]=[C:10]([CH:12]=[CH:13][C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1.[O:23]1CCOCC1>[OH-].[Na+]>[NH2:1][C:2]1[N:3]=[C:4]([OH:23])[C:5]2[CH:11]=[C:10]([CH:12]=[CH:13][C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 54082773HCID 54082773, compound

Product 1

HCID 178508856HCID 178508856, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
24 °C

Procedure

A suspension of 0.4 g (1.2 mM) of 2,4-diamino-6-[2-(3,5-dichlorophenyl)ethenyl]pyrido[2,3-d]pyrimidine (prepared as described in Example 3), in 80 ml of 1N sodium hydroxide was heated at reflux for 24 hours. Since not all the starting material had dissolved, 10 ml of 5N sodium hydroxide and 25 ml of dioxane were added, and the mixture was heated at reflux for an additional 24 hours. The reaction mixture was cooled to 24° C., filtered, and the filtrate was diluted with 30 ml of glacial acetic acid. The precipitate which formed was collected by filtration, washed with 50 ml of water, and then with 50 ml of diethyl ether, and dried at 100° C. under vacuum to provide 160 mg of 2-amino-4-hydroxy-6-[2-(3,5-dichlorophenyl)ethenyl]pyrido-[2,3-d]pyrimidine.

Workup

  1. temperatureat reflux for 24 hours
  2. dissolutionSince not all the starting material had dissolved
  3. temperaturethe mixture was heated
  4. temperatureat reflux for an additional 24 hours
  5. filtrationfiltered
  6. additionthe filtrate was diluted with 30 ml of glacial acetic acid
  7. customThe precipitate which formed
  8. filtrationwas collected by filtration
  9. washwashed with 50 ml of water
  10. dry with materialwith 50 ml of diethyl ether, and dried at 100° C. under vacuum

Sources & evidence

ORD record
ord-10338759828a4d47936aa59e7040e3c9
Source dataset
uspto-grants-1993_06
Patent number
US05223503

Reaction notes

Loading…