4-Ethoxyaniline → 6-(2,6-Dichlorophenyl)-2-(4-ethoxyphenylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3205

Reaction equation

HRID 3205 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH2:24][CH3:25])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH2:26]([O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)[CH3:27]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH2:24][CH3:25])[C:12]2[N:13]=[C:14]([NH:33][C:32]3[CH:34]=[CH:35][C:29]([O:28][CH2:26][CH3:27])=[CH:30][CH:31]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

5

Reactant 2

HCID 90764-EthoxyanilineHCID 105969946-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 116194226-(2,6-Dichlorophenyl)-2-(4-ethoxyphenylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 0.150 g (0.38 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 68 and 0.500 g (3.60 mmol) of 4-ethoxyaniline was fused in a 160° C. oil bath for 10 minutes. The dark violet melt was cooled and dissolved in 1 mL of warm glacial acetic acid. This solution was diluted to 10 mL volume with water to precipitate a solid. The solid was filtered, washed well with water, and dried; wt 0.140 g. Purification was effected by filtration of an ethyl acetate solution through a layer of silica gel and washing the silica gel with ethyl acetate. The filtrate was concentrated to 2 mL volume and 2 mL of petroleum ether was added. The crystals that separated on inducement were filtered and washed with ether; wt 0.094 g; mp 192°-194° C.

Workup

  1. customwas fused in a 160° C.
  2. customfor 10 minutes
  3. temperatureThe dark violet melt was cooled
  4. customto precipitate a solid
  5. filtrationThe solid was filtered
  6. washwashed well with water
  7. customdried
  8. customPurification
  9. filtrationwas effected by filtration of an ethyl acetate solution through a layer of silica gel
  10. washwashing the silica gel with ethyl acetate
  11. concentrationThe filtrate was concentrated to 2 mL volume and 2 mL of petroleum ether
  12. additionwas added
  13. customThe crystals that separated on inducement
  14. filtrationwere filtered
  15. washwashed with ether

Sources & evidence

ORD record
ord-e03019db057645d990f6974409cc35bc
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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