Aniline → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, 6-methyl-4-oxo-N-phenyl-

HRID 273714Notes

Reaction equation

HRID 273714 reaction equation
[CH3:1][C:2]1[N:7]2[C:8](=[O:15])[C:9]([C:12]([OH:14])=O)=[CH:10][N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OC)=O.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[C:29]1([NH:28][C:12]([C:9]2[C:8](=[O:15])[N:7]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]3=[N:11][CH:10]=2)=[O:14])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 2084164H-Pyrido(1,2-a)pyrimidine-3-carboxylic acid, 6-methyl-4-oxo-

Product 1

HCID 30792874H-Pyrido(1,2-a)pyrimidine-3-carboxamide, 6-methyl-4-oxo-N-phenyl-Yield 78.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 16.32 g (0.08 mol) of 6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and 12.4 ml (0.088 mol) of triethylamine in 480 ml of chloroform is cooled below -10° C. by ice-salt. A solution of 6.5 ml (0.08 mol) of methyl chloroformate in 40 ml of chloroform is dropped to the above mixture at a temperature between -10° C. and -13° C. during 20 minutes. After stirring for 5 minutes, 9.19 g (0.088 mol) of aniline dissolved in 80 ml of chloroform are dropped to the above solution at a temperature between -10° C. and -13° C. during 30 minutes. The reaction mixture is stirred below -10° C. for 1 hour and then allowed to stand overnight under cooling by ice. For working up, the reaction mixture is washed 3 times with 150 ml of 5% sodium hydrogen carbonate solution each and then 3 times with 150 ml of water each. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated to give 17.6 g (78.8%) of the named compound as yellow crystals after recrystallization from ethanol, m.p.: 186°-188° C.

Workup

  1. additionare dropped to the above solution at a temperature between -10° C. and -13° C. during 30 minutes
  2. stirringThe reaction mixture is stirred below -10° C. for 1 hour
  3. waitto stand overnight
  4. temperatureunder cooling by ice
  5. washthe reaction mixture is washed 3 times with 150 ml of 5% sodium hydrogen carbonate solution each and then 3 times with 150 ml of water each
  6. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6586c9589936424cb13c65071241ee49
Source dataset
uspto-grants-1995_02
Patent number
US05387588

Reaction notes

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