Methyl chloroformate → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, 8-methyl-4-oxo-N-propyl-

HRID 273719Notes

Reaction equation

HRID 273719 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][N:5]2[C:6](=[O:13])[C:7]([C:10]([OH:12])=O)=[CH:8][N:9]=[C:4]2[CH:3]=1.C(N(CC)CC)C.ClC(OC)=O.[CH2:28]([NH2:31])[CH2:29][CH3:30]>C(Cl)(Cl)Cl>[CH2:28]([NH:31][C:10]([C:7]1[C:6](=[O:13])[N:5]2[CH:14]=[CH:15][C:2]([CH3:1])=[CH:3][C:4]2=[N:9][CH:8]=1)=[O:12])[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 7852PropylamineHCID 8471TriethylamineHCID 28008748-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid

Product 1

HCID 30792924H-Pyrido(1,2-a)pyrimidine-3-carboxamide, 8-methyl-4-oxo-N-propyl-Yield 88.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 16.32 g (0.08 mol) of 8-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 dissolved in 40 ml of chloroform is dropped to the above mixture at -18° C. during 10 minutes. After stirring for 5 minutes, 5.2 g (0.088 mol) of propylamine dissolved in 80 ml of chloroform are dropped to the above solution at -18° C. during 60 minutes. The reaction mixture is stirred at -10° C. for 1 hour, then allowed to stand under cooling by ice. For working up, the reaction mixture is washed 3 times with 150 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 150 ml of water each. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated to give 17.3 g (88.2%) of the named compound as yellow crystals after recrystallization from ethanol, m.p.: 194°-196° C.

Workup

  1. temperatureis cooled below -10° C. by ice salt
  2. additionis dropped to the above mixture at -18° C. during 10 minutes
  3. additionare dropped to the above solution at -18° C. during 60 minutes
  4. stirringThe reaction mixture is stirred at -10° C. for 1 hour
  5. temperatureunder cooling by ice
  6. washthe reaction mixture is washed 3 times with 150 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 150 ml of water each
  7. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-d3c741c68e9f415da0c59c19a674a8bd
Source dataset
uspto-grants-1995_02
Patent number
US05387588

Reaction notes

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