Hydrochloric Acid → 6-(2-bromo-6-chlorophenyl)-8-ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3226Notes

Reaction equation

HRID 3226 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:25](=N)[N:24]([CH2:27][CH3:28])[C:12]2[N:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1.C(OC(=O)C)(=[O:31])C.Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:25](=[O:31])[N:24]([CH2:27][CH3:28])[C:12]2[N:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 18934792HCID 18934792, compound

Product 1

HCID 115833536-(2-bromo-6-chlorophenyl)-8-ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(6-(2-Bromo-6-chlorophenyl)-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine (150 mg) was added to 1 mL of acetic anhydride and heated at reflux for 5 minutes. The reaction was cooled and concentrated resulting in an oil which was heated at reflux with 10 mL of 6N HCl for 10 minutes. The reaction was cooled, and 30 mL of water was added causing precipitation. The precipitate was removed by filtration and washed with water. The resulting solid was dried to give 130 mg of 6-(2-bromo-6-chlorophenyl)-8-ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one; mp softens at 195° C. and melts at 210°-214° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 minutes
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. customresulting in an oil which
  6. temperaturewas heated
  7. temperatureThe reaction was cooled
  8. customprecipitation
  9. customThe precipitate was removed by filtration
  10. washwashed with water
  11. customThe resulting solid was dried

Sources & evidence

ORD record
ord-8101dbefc33b4ad5952d74a7f2f862b6
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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