Aniline → 9-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester

HRID 443392Notes

Reaction equation

HRID 443392 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:18])[CH2:14][CH:15]=[C:16](O)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:18])[CH2:14][CH:15]=[C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 13131707HCID 13131707, compound

Product 1

HCID 133694119-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl esterYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 g. (2.00 mmoles) of 9-hydroxy-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester is dissolved in 5 ml. of anhydrous ethanol. To the solution 0.3 g. (3.00 mmoles) of aniline is added and the solution is heated under reflux for 3 hours. The reaction mixture is then cooled and the precipitated crystals are filtered and washed with some ethanol. 0.3 g. (46.1%) of 9-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester is obtained, melting point: 119°-120° C.

Workup

  1. temperaturethe solution is heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture is then cooled
  4. filtrationthe precipitated crystals are filtered
  5. washwashed with some ethanol

Sources & evidence

ORD record
ord-1cbd73a685164c97b25a6563f4b4f4bd
Source dataset
uspto-grants-1981_04
Patent number
US04260612

Reaction notes

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