Acetic Anhydride → N-[6-(3,5-Dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylidene]-acetamide

HRID 1793879Notes

Reaction equation

HRID 1793879 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:22](=[NH:23])[N:21]([CH2:24][CH3:25])[C:14]3[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>COC(C)(C)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[C:22](=[N:23][C:26](=[O:28])[CH3:27])[N:21]([CH2:24][CH3:25])[C:14]3[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 222201776-(3,5-Dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine2×

Product 1

HCID 21021924N-[6-(3,5-Dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylidene]-acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of the product of Example 4, 6-(3,5-dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine (50.0 g, 0.145 mol), and acetic anhydride (150 mL) were heated with stirring until reflux at which point all the starting material dissolved. The reaction mixture was heated at reflux for 5 minutes, cooled in an ice bath, and t-butyl methyl ether added. The product was collected by filtration, washed with acetic anhydride (50 mL) and ether (100 mL) to afford 43.7 g (78% yield) of the titled compound. mp 145–150° C.

Workup

  1. temperaturewere heated
  2. temperatureuntil reflux at which point all the starting material
  3. dissolutiondissolved
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 5 minutes
  6. temperaturecooled in an ice bath
  7. filtrationThe product was collected by filtration
  8. washwashed with acetic anhydride (50 mL) and ether (100 mL)

Sources & evidence

ORD record
ord-83a2cebc2c6f4d58a1541cc30df5e320
Source dataset
uspto-grants-2006_04
Patent number
US07022711B2

Reaction notes

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