Cyclopentylamine → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-cyclopentyl-8-methyl-4-oxo-

HRID 273725Notes

Reaction equation

HRID 273725 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.[CH:28]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1>C(Cl)(Cl)Cl>[CH:28]1([NH:33][C:10]([C:7]2[C:6](=[O:13])[N:5]3[CH:14]=[CH:15][C:2]([CH3:1])=[CH:3][C:4]3=[N:9][CH:8]=2)=[O:12])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 28008748-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid

Product 1

HCID 30793024H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-cyclopentyl-8-methyl-4-oxo-Yield 55.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 1.22 g (0.006 mol) of 8-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 -15° 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. 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 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 yield 0.9 g (55%) of the named compound as a crystalline substance after recrystallization from ethanol, m.p.: 220°-222° C.

Workup

  1. additionis dropped to the above solution
  2. stirringThe reaction mixture is 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-0b576cdbfaa1417e94b57892d3fc8ab8
Source dataset
uspto-grants-1995_02
Patent number
US05387588

Reaction notes

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