Acetic Anhydride → N-[6-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-ylidene]acetamide

HRID 3174Notes

Reaction equation

HRID 3174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[NH:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=2[CH:10]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[N:21][C:23](=[O:25])[CH3:24])[N:19]([CH3:22])[C:12]2[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 108078276-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-imine

Product 1

HCID 10596723N-[6-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-ylidene]acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.161 g (0.46 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3 -d]pyrimidin-7-ylideneamine from Example 19 and 1.0 mL of acetic anhydride was heated to solution at the boiling point. After 2 minutes of reflux, the solution was concentrated to one-half volume, whereupon crystals formed. The mixture was cooled, 2 mL of ether was added, and the product was filtered and washed with ether; mp 229°-231° C.

Workup

  1. temperaturewas heated to solution at the boiling point
  2. temperatureAfter 2 minutes of reflux
  3. concentrationthe solution was concentrated to one-half volume, whereupon crystals
  4. customformed
  5. temperatureThe mixture was cooled
  6. filtrationthe product was filtered
  7. washwashed with ether

Sources & evidence

ORD record
ord-de9b6ae759eb4e73bdbda8a0c8140fe5
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

Loading…