P-Anisidine → 6-(2,6-Dichlorophenyl)-2-(4-methoxyphenylamino)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3199

Reaction equation

HRID 3199 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]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH3:25][O:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>>[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]([CH3:24])[C:12]2[N:13]=[C:14]([NH:31][C:30]3[CH:32]=[CH:33][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 53278966-(2,6-Dichlorophenyl)-2-(4-methoxyphenylamino)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

Conditions

Temperature
180 °C

Procedure

A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.50 g (4.10 mmol) of 4-methoxyaniline was heated, with stirring, in a 180° C. oil bath. The resulting solution was heated for 10 minutes. Much of the excess aniline was evaporated at reduced pressure. The remainder was dissolved in 2 mL of ethyl acetate. The crystals that separated from the dark solution were filtered and washed with 2 mL of ethyl acetate, wt 0.102 g.

Workup

  1. temperaturewas heated
  2. temperatureThe resulting solution was heated for 10 minutes
  3. customMuch of the excess aniline was evaporated at reduced pressure
  4. dissolutionThe remainder was dissolved in 2 mL of ethyl acetate
  5. customThe crystals that separated from the dark solution
  6. filtrationwere filtered
  7. washwashed with 2 mL of ethyl acetate, wt 0.102 g

Sources & evidence

ORD record
ord-2385e0240fd44243a34f8caa93efa84f
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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