Methyl chloroformate → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, 7-methyl-4-oxo-N-propyl-

HRID 273718Notes

Reaction equation

HRID 273718 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:15]=1)[C:7](=[O:14])[C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=2.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:11]([C:8]1[C:7](=[O:14])[N:6]2[CH:15]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)=[O:13])[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 7852PropylamineHCID 8471TriethylamineHCID 87681627-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid

Product 1

HCID 30792914H-Pyrido(1,2-a)pyrimidine-3-carboxamide, 7-methyl-4-oxo-N-propyl-Yield 89.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 16.32 g (0.08 mol) of 7-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 20 minutes. After stirring for 5 minutes, 5.2 (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 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, then 3 times with 150 ml of water each. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated to obtain 17.5 g (89.2%) of the named compound as yellow crystals after recrystallization from ethanol, m.p.: 126°-128° C.

Workup

  1. additionis dropped to the above mixture at -18° C. during 20 minutes
  2. additionare dropped to the above solution at -18° C. during 60 minutes
  3. stirringThe reaction mixture is stirred at -10° C. for 1 hour
  4. waitto stand overnight
  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-c8cb3693f8ac4eeb8e3a1d3d0c7555e8
Source dataset
uspto-grants-1995_02
Patent number
US05387588

Reaction notes

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