Hydrochloric Acid → 8-ethyl-6-naphthalen-2-yl-2-phenylamino-8H-pyrido[2,3-d]-pyrimidin-7-one

HRID 3235Notes

Reaction equation

HRID 3235 reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:4]1=N)[CH3:2].C(OC(=O)C)(=[O:33])C.Cl>O>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:4]1=[O:33])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 11710876(8-Ethyl-7-imino-6-naphthalen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine

Product 1

HCID 115384008-ethyl-6-naphthalen-2-yl-2-phenylamino-8H-pyrido[2,3-d]-pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(8-Ethyl-7-imino-6-naphthalen-2-yl-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 2 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 40 mL of water was added causing precipitation. The precipitate was removed by filtration and washed with water. The resulting solid was dried in a vacuum oven to provide 8-ethyl-6-naphthalen-2-yl-2-phenylamino-8H-pyrido[2,3-d]-pyrimidin-7-one; mp 254°-256° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 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 in a vacuum oven

Sources & evidence

ORD record
ord-bbffcf2db8554d41a139114578bcbcd5
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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