Cyclopentylamine → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-cyclopentyl-7-methyl-4-oxo-

HRID 467030Notes

Reaction equation

HRID 467030 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.[CH:28]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1>C(Cl)(Cl)Cl>[CH:28]1([NH:33][C:11]([C:8]2[C:7](=[O:14])[N:6]3[CH:15]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)=[O:13])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 87681627-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid

Product 1

HCID 30793014H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-cyclopentyl-7-methyl-4-oxo-Yield 49.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 1.22 g (0.006 mol) of 7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and 0.84 ml (0.006 mol) of triethylamine in 40 ml of chloroform is cooled below -10° C. by ice-salt. A solution of 0.46 ml (0.006 mol) of methyl chloroformate in 3 ml of chloroform is dropped to the above mixture at -18° C. during 10 minutes. After stirring for 5 minutes, 0.56 g (0.0066 mol) of cyclopentylamine dissolved in 6 ml of chloroform is dropped to the above solution which is then stirred at -10° C. for 1 hour and allowed to stand overnight under cooling by ice. For working up, the reaction mixture is washed 3 times with 15 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 15 ml of water each. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated to give 0.8 g (49.2%) of the named compound as white crystals after recrystallization from ethanol, m.p.: 162°-164° C.

Workup

  1. additionis dropped to the above solution which
  2. stirringis then stirred at -10° C. for 1 hour
  3. waitto stand overnight
  4. temperatureunder cooling by ice
  5. washthe reaction mixture is washed 3 times with 15 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 15 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-b9081e1e79184b64b4e12f36f338561d
Source dataset
uspto-grants-1992_10
Patent number
US05158951

Reaction notes

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