3,4,5-Trimethoxyaniline → 6-(2,6-Dichlorophenyl)-8-ethyl-2-(3,4,5-trimethoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3207

Reaction equation

HRID 3207 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.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[NH2:31]>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:31][C:30]3[CH:32]=[C:33]([O:37][CH3:38])[C:34]([O:35][CH3:36])=[C:28]([O:27][CH3:26])[CH:29]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

5

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 105969946-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 115406076-(2,6-Dichlorophenyl)-8-ethyl-2-(3,4,5-trimethoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

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 (2.70 mmol) of 3,4,5-trimethoxyaniline was heated in a 160° C. oil bath for 5 minutes. The dark solution was cooled and dissolved in 2 mL of warm glacial acetic acid. This solution was diluted to 15 mL volume with water to precipitate a violet solid. The solid was filtered, washed well with water, and dried; wt 0.140 g. Purification was effected by filtration of an ethyl acetate (30 mL) solution through a layer of silica gel and washing the silica gel with ethyl acetate. The filtrate was concentrated to 3 mL volume. The crystals that separated on inducement were filtered and washed with 1 mL of ethyl acetate and 1 mL of ether; wt 0.054 g; mp 275°-278° C.

Workup

  1. temperatureThe dark solution was cooled
  2. customto precipitate a violet solid
  3. filtrationThe solid was filtered
  4. washwashed well with water
  5. customdried
  6. customPurification
  7. filtrationwas effected by filtration of an ethyl acetate (30 mL) solution through a layer of silica gel
  8. washwashing the silica gel with ethyl acetate
  9. concentrationThe filtrate was concentrated to 3 mL volume
  10. customThe crystals that separated on inducement
  11. filtrationwere filtered
  12. washwashed with 1 mL of ethyl acetate and 1 mL of ether

Sources & evidence

ORD record
ord-76f6a432b29140da8181c2f2c78550f6
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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