Methyl chloroformate → 4H-Pyrido(1,2-a)pyrimidine-3-acetamide, 6-methyl-4-oxo-N-propyl-

HRID 273721Notes

Reaction equation

HRID 273721 reaction equation
[CH3:1][C:2]1[N:7]2[C:8](=[O:16])[C:9]([CH2:12][C:13]([OH:15])=O)=[CH:10][N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OC)=O.[CH2:29]([NH2:32])[CH2:30][CH3:31]>C(Cl)(Cl)Cl>[CH2:29]([NH:32][C:13](=[O:15])[CH2:12][C:9]1[C:8](=[O:16])[N:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]2=[N:11][CH:10]=1)[CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 7852PropylamineHCID 8471TriethylamineHCID 5993036-Methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-acetic acid

Product 1

HCID 30792944H-Pyrido(1,2-a)pyrimidine-3-acetamide, 6-methyl-4-oxo-N-propyl-Yield 30.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 2.18 g (0.01 mol) of 6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-acetic acid and 1.55 ml (0.011 mol) of triethylamine in 60 ml of chloroform is cooled below -10° C. by ice-salt. A solution of 0.945 g (0.01 mol) of methyl chloroformate in 5 ml of chloroform is dropped to the above mixture at -12° C. during 7 minutes. After stirring for 5 minutes, 0.65 g (0.011 mol) of propylamine dissolved in 10 ml of chloroform is dropped to the above solution at -15° C. during 10 minutes. The reaction mixture is stirred at -15° C. for 1 hour, then allowed to stand overnight under cooling by ice. For working up, the reaction mixture is washed 3 times with 40 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 40 ml of water each. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated. Alter thoroughly triturating the residue with cold ethyl acetate, 0.8 g (30.9%) of the named compound is obtained, m.p.: 96°-98° C. after recrystallization from ethyl acetate.

Workup

  1. additionis dropped to the above solution at -15° C. during 10 minutes
  2. stirringThe reaction mixture is stirred at -15° C. for 1 hour
  3. waitto stand overnight
  4. temperatureunder cooling by ice
  5. washthe reaction mixture is washed 3 times with 40 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 40 ml of water each
  6. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customAlter thoroughly triturating the residue with cold ethyl acetate

Sources & evidence

ORD record
ord-e1e18e4564b047cf92f02edfe39bbc99
Source dataset
uspto-grants-1995_02
Patent number
US05387588

Reaction notes

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