Diglyme → 6-(2,6-Dichlorophenyl)-2-((4-(2-(diethylamino)ethoxy)phenyl)amino)-8-methylpyrido(2,3-d)pyrimidin-7(8H)-one

HRID 3209

Reaction equation

HRID 3209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH2:23]([N:25]([CH2:36][CH3:37])[CH2:26][CH2:27][O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)[CH3:24].COCCOCCOC>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14]([NH:33][C:32]3[CH:31]=[CH:30][C:29]([O:28][CH2:27][CH2:26][N:25]([CH2:36][CH3:37])[CH2:23][CH3:24])=[CH:35][CH:34]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 8150DiglymeHCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 53113826-(2,6-Dichlorophenyl)-2-((4-(2-(diethylamino)ethoxy)phenyl)amino)-8-methylpyrido(2,3-d)pyrimidin-7(8H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.155 g (0.40 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 0.167 g (0.80 mmol) of 4-(2-diethylaminoethoxy)aniline and 1 mL of (2-methoxyethyl)ether (bp 162° C.) was heated with stirring in a 150° C. oil bath. All solid gradually dissolved over a period of 10 minutes. The solution was heated another 10 minutes and cooled to 100° C. Water was added dropwise until slight turbidity. The crystals that separated on inducement were filtered, washed with 0.5 mL of ether and 2 mL of water, and dried; wt 0.105 g. Purification was effected by chromatography eluting with chloroform, then ethyl acetate and finally 10% methanol/chloroform to obtain fraction with pure product. The eluent was evaporated to dryness. The remaining amorphous solid was dissolved in 1 mL of warm ethyl acetate. The crystals that separated on inducement were filtered and washed sparingly with ethyl acetate and ether; wt 0.042 g; mp 141°-143° C.

Workup

  1. temperaturewas heated
  2. dissolutionAll solid gradually dissolved over a period of 10 minutes
  3. temperatureThe solution was heated another 10 minutes
  4. temperaturecooled to 100° C
  5. customThe crystals that separated on inducement
  6. filtrationwere filtered
  7. washwashed with 0.5 mL of ether and 2 mL of water
  8. customdried
  9. customPurification
  10. washeluting with chloroform
  11. customethyl acetate and finally 10% methanol/chloroform to obtain fraction with pure product
  12. customThe eluent was evaporated to dryness
  13. dissolutionThe remaining amorphous solid was dissolved in 1 mL of warm ethyl acetate
  14. customThe crystals that separated on inducement
  15. filtrationwere filtered
  16. washwashed sparingly with ethyl acetate and ether

Sources & evidence

ORD record
ord-0ccd6005f4ca42f39fa580909f4210c7
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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