Aniline → 2-aminopyrido[2,3-d]pyrimidin-7(8H)-one 39

HRID 3201

Reaction equation

HRID 3201 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.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[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]([CH2:24][CH3:25])[C:12]2[N:13]=[C:14]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 105969946-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 53278862-aminopyrido[2,3-d]pyrimidin-7(8H)-one 39

Conditions

Temperature
195 °C

Procedure

A mixture of 0.134 g (0.33 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 (5.40 mmol) of aniline was heated with stirring in a 195° C. oil bath to reflux. The resulting solution was maintained at reflux for 5 minutes. Most of the excess aniline was evaporated at reduced pressure. The residual gum was dissolved in 15 mL of ethyl acetate. After filtration of a relatively small amount of insoluble material, the solution was filtered through a layer of silica gel to remove violet color. The filtrate was concentrated to 2 mL volume. Petroleum ether was added until slight turbidity. The crystals that separated on inducement were filtered and washed with 50% ether/petroleum ether; wt 0.068 g; mp 223°-225° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe resulting solution was maintained
  4. temperatureat reflux for 5 minutes
  5. customMost of the excess aniline was evaporated at reduced pressure
  6. dissolutionThe residual gum was dissolved in 15 mL of ethyl acetate
  7. filtrationAfter filtration of a relatively small amount of insoluble material
  8. filtrationthe solution was filtered through a layer of silica gel
  9. customto remove violet color
  10. concentrationThe filtrate was concentrated to 2 mL volume
  11. additionPetroleum ether was added until slight turbidity
  12. customThe crystals that separated on inducement
  13. filtrationwere filtered
  14. washwashed with 50% ether/petroleum ether

Sources & evidence

ORD record
ord-4ca4e30594e44f88b0f99fc7322a410a
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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