Cyclohexylamine → 2-Cyclohexylamino-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3197

Reaction equation

HRID 3197 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.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH:25]1([NH:31][C:14]2[N:15]=[CH:16][C:11]3[CH:10]=[C:9]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])[C:22](=[O:23])[N:21]([CH3:24])[C:12]=3[N:13]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 53278722-Cyclohexylamino-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

Conditions

Temperature
134 °C

Procedure

A mixture of 0.100 g (0.26 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.300 g (3.00 mmol) of cyclohexylamine was heated to the boiling point (134° C.). The resulting solution was heated at reflux for 2 minutes. Most of the excess amine was evaporated at reduced pressure. The remaining gum was dissolved in 2 mL of ethyl acetate hot. Petroleum ether (2 mL) was added, and the crystals that separated from the cooled solution were filtered and washed with water; wt 0.090 g. Recrystallization from ethyl acetate gave pure crystalline product; 0.048 g; mp 242°-244° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 2 minutes
  3. customMost of the excess amine was evaporated at reduced pressure
  4. dissolutionThe remaining gum was dissolved in 2 mL of ethyl acetate hot
  5. additionPetroleum ether (2 mL) was added
  6. customthe crystals that separated from the cooled solution
  7. filtrationwere filtered
  8. washwashed with water
  9. customRecrystallization from ethyl acetate
  10. customgave pure crystalline product

Sources & evidence

ORD record
ord-3191b5ba687c4a38ba69160188ee969d
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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